Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-05 Chun-Yang Zhao, Kun Li, Yu Pang, Jia-Qing Li, Cui Liang, Gui-Fa Su, Dong-Liang Mo
A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline.
Gold-Catalyzed Intramolecular Dearomatization of Phenols with Allenoates for the Synthesis of Spirocyclohexadienones Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-15 Hongyu Wang, Kaiye Wang, Yanan Xiang, Han Jiang, Xiuyan Wan, Na Li, Bo Tang
The first example of the efficient synthesis of spirocyclohexadienones via the dearomatization of phenols involving allenoates catalyzed by Au(I) was reported. Moreover, the intermolecular remote-Rauhut-Currier reaction between allenoates and para-quinones catalyzed by nucleophilic phosphines was also realized.
Isocoumarin: General aspects and recent advances in the synthesis Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-14 Pallabi Saikia, Sanjib Gogoi
Being an important constituent of naturally occurring lactones with diverse biological activities and as a pivotal intermediate in heterocycle synthesis, isocoumarin has claimed vast interests in synthetic and medicinal research. The methodologies for the synthesis of isocoumarins involve particularly the metal-catalyzed reactions as well as various intramolecular and intermolecular cyclization reactions. The transition metal complexes of Pd, Cu, Rh, Ru, Ir, Ni, Zn and Ag are frequently used for the construction of this scaffold. The electrophilic cyclization, oxyboration, iodocyclization reactions are also known to afford isocoumarins. This review article attempts to highlight the recent advances on the synthesis along with the general aspects such as natural occurrence, biological activities etc of this particular heterocyclic scaffold.
Lewis-acid Promoted Chemoselective Condensation of 2-Aminobenzimidazoles or 3-Aminoindazoles with 3-Ethoxycyclobutanones to Construct Fused Nitrogen Heterocycles Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-14 Weiguang Kong, Yao Zhou, Qiuling Song
A Lewis-acid promoted chemoselective condensation of 2-aminobenzimidazoles or 3-aminoindazoles with 3-ethoxycyclobutanones is presented. Diverse fused heterocycles benzo[4,5]-imidazo[1,2-a]pyrimidine and pyrimido[1,2-b]-indazole derivatives were obtained in moderate to high yields under mild conditions, the reaction mechanism of which was in sharp contrast to previous [3+3] annulation reaction of 3-ethoxycyclobutanones.
Additive Controlled Switchable Selectivity from Cyanobenzenes to 2-Alkynylpyridines: Ruthenium(II) Catalyzed [2+2+2] Cycloadditions of Diynes and Alkynylnitriles Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-14 Divya Bhatt, Neha Patel, Hrishikesh Chowdhury, Prasad V Bharatam, Avijit Goswami
A highly efficient additive dependent chemo- selective protocol for the synthesis of fused cyanoarenes and 2-alkynylpyridines has been developed by the reaction of 1,6-diynes with alkynylnitriles using chloro (pentamethylcyclopentadienyl) (cyclooctadiyne)ruthenium (II) as a catalyst in dimethoxyethane (DME). The course of the reaction can be drastically altered simply by adding catalytic amount of AgOTf as an additive resulting in a comprehensible shift in product formation from cyanoarenes to 2-alkynylpyridines. Theoretical studies clearly indicate that the neutral Ru-complex is responsible for the formation of cyanobenzenes, whereas, cationic Ru-complex generated in-situ plays a crucial role for the 2-alkynylpyridines formation.
Silver-Catalyzed Isocyanide Insertion into N–H Bond of Ammonia: [5 + 1] Annulation to Quinazoline Derivatives Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-14 Lingjuan Zhang, Juanjuan Li, Zhongyan Hu, Jinhuan Dong, Xian-Ming Zhang, Xianxiu Xu
A silver-catalyzed [5 + 1] annulation of o-acylaryl isocyanides with ammonium acetate and hydroxlamine was developed for the efficient and practical synthesis of quinazolines and quinazoline 3-oxides in good to excellent yields, respectively. The domino process involved an unprecedented isocyanide insertion into the N−H bond of ammonia or hydroxylamine and followed by condensation reaction at ambient conditions.
Palladium-Catalyzed Decarboxylative Cross-Couplings of 1-Boc-3-iodoazetidine: Regioselective Access to 2-Alkynylazetidines, 3-Alkynylazetidines and 3-Vinylazetidines Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-13 Shuaijun Han, Xiaoxiao Ren, Qingsong Wu, Apeng Liang, jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu
The first palladium-catalyzed decarboxylative coupling reactions of alkynyl carboxylic acids or α, β-unsaturated carboxylic acids with 1-Boc-3-iodoazetidine were described. The strategy could efficiently mediate β-hydride elimination/migratory insertion sequence and selectively form 2-alkynylazetidines (10 examples) and 3-alkynylazetidines (15 examples) with high regioselectivity. The protocol provides convienient access to a variety of useful 3-vinylazetidines in moderate yields (42 %-72 %) with good stereoselectivity. Notable advantages of this method include easy operation, mild reaction conditions, and wide substrate scope.
Divergent Synthesis of Quinoline Derivatives via [5+1] Annulation of 2-Isocyanochalcones with Nitroalkanes Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-13 Lan Bao, Jinglin Liu, Liang Xu, Zhongyan Hu, Xianxiu Xu
An unprecedented substrate-dependent [5+1] annulation of 2-isocyanochalcones with nitroalkanes was developed for the efficient synthesis of functionalized quinolines and 3-nitrodihydroquinolines. This transformation delivers both the aromatic and dihydroquinolines by selectively elimination or retention of the nitro group. Moreover, 3-nitroquinolines and tricyclic pyrrolo[2,3-c]quinolines were conveniently constructed from the resulting 3-nitrodihydroquinolines through a single operation, respectively.
Recent Advances on Amino Acid Modifications via C-H-Functionalization and Decarboxylative functionalization Strategies Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-13 Santanu Mondal, Sushobhan Chowdhury
Over the recent decade tremendous interest has been developed on the synthetic modification of natural as well as nonproteinogenic amino acids and non-natural linkages due to their immense important applications in proteomics, diagnosis, and drug delivery etc. They are synthetically important also. For example, due to the high natural abundance of enantiopure amino acids, they and their derivatives are regularly employed in the development of several interesting synthetic methods, total syntheses of biologically related structures as well as in ligand elaboration. Thus, the synthetic field possess a direct impact on several basic and applied sciences. But till date only limited number of reviews are available which either appeared almost half decade earlier or covered very specific areas of this highly expanding topic. A lot of achievements has already been done in this field in the meantime which are needed to be documented urgently. Therefore, to meet the need this review is written which covers the emerging versatile synthetic methods on the modification of amino acids and related structures over the recent decade with the relevant details of their respective prospects and problems in the best possible systematic concise manner. Wherever needed relevant mechanistic details are also described.
Recent Advances in C−B Bond Formation through a Free Radical Pathway Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-12 Guobing Yan, Dayun Huang, Xiangmei Wu
C70 Fullerene-Catalyzed Metal-Free Photocatalytic ipso-Hydroxylation of Aryl Boronic Acids: Synthesis of Phenols Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-11 Inder Kumar, Ritika Sharma, Rakesh Kumar, Rakesh Kumar, Upendra Sharma
A metal-free C70 fullerene-catalyzed method has been developed for the ipso-hydroxylation of aryl and heteroaryl boronic acids to corresponding phenols under photocatalytic conditions. The reaction proceeds under oxygen atmosphere and the mechanistic study revealed that C70 plays a critical role in the generation of reactive oxygen species in the presence of blue light. Reactions in the presence of 18O-labelled water and oxygen confirmed the generation of reactive oxygen species from oxygen molecule.Amine used as a reductant could be recovered in the form of imine. The current method is also applicable to the synthesis of aryl ethers in one-pot two-step process.
Palladium-Catalyzed Cascade C-O Cleavage and C-H Alkenylation of Phosphinyl Allenes: An Expeditious Approach to 3-Alkenyl Benzo[b]phosphole Oxides Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-11 Teng Liu, Xue Sun, Lei Wu
A phosphine oxide-directed intramolecular cyclization of phosphinyl allenes is established for the first time. The palladium-catalyzed intramolecular cyclization provides an unprecedented cascade C-O cleavage and direct C-H alkenylation toward novel 3-alkenyl benzo[b]phosphole oxides, along with broad group tolerance and highly regioselectivity. Control experiments and mechanistic studies explain the sequential performance of C(sp3)-OAr cleavage and P=O directed C(sp2)-H activation.
Rapid Formation of Fluoren-9-ones via Palladium-Catalyzed External Carbon Monoxide-Free Carbonylation Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-10 Hideyuki Konishi, Suguru Futamata, Xi Wang, Kei Manabe
A Pd-catalyzed carbonylation reaction for the synthesis of fluoren-9-ones from 2-halogenated biphenyls using phenyl formate as a carbon monoxide surrogate was achieved. The combined use of cesium carbonate and <i>o</i>-anisic acid resulted in a remarkable rate enhancement, where the reaction was complete within 3 min in some cases. Mechanistic studies indicated that the turnover-limiting step of the reaction was the C–H bond-cleaving step or the oxidative addition step, depending on the substrate used.
Nickel catalyzed ipso-hydroxylation and subsequent cross dehydrogenative coupling of arylboronic acids with tertiary amines: A facile access to α-phenolated tertiary amines Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-10 Promod Kumar, Anup Kumar Sharma, Rahul Singh, Tirumaleswararao Guntreddi, Krishna Nand Singh
A straightforward and new approach has been developed for the α-functionalization of tertiary amines via sequential oxidative hydoxylation and cross-dehydrogenative coupling (CDC) of arylboronic acids with tertiary amines to afford α-phenolated tertiary amines. The results demonstrate an easy arylation of C(sp3)–H bond in the presence of an inexpensive and readily available nickel metal salt.
Controlled Transformations of Aryl Halides in a Flow System: Selective Synthesis of Aryl Azides and Aniline Derivatives Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-09 Adam Georgiades, Sandor Otvos, Ferenc Fülöp
Abstract. Copper-mediated nitrogenation of aryl halides with sodium azide can result in either aryl azides or aniline derivatives. The selectivity of the transformation is highly dependent on reaction time and temperature, which led to contradictory literature results with respect to product selectivity and the conditions applied. The advantages of a strictly controlled flow reactor environment were exploited in order to facilitate selective haloarene transformations. Reaction conditions were carefully investigated to understand their role on product selectivity.Aryl azides and aryl amines were successfully prepared from the same starting materials using the same auxiliaries by means of precise control over residence time and reaction temperature, thereby ensuring time-, cost- and atom-efficient syntheses.
Electrochemical C−S Bond Formation by a Dual Catalytic System Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-09 Sen Liang, Cheng-Chu Zeng, Hong-Yu Tian, Bao-Guo Sun, Xu-Gang Luo, Fa-zheng Ren
Terpene-Derived Highly Branched C30-Amines via Palladium-Catalysed Telomerisation of Farnesene Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-07 Dennis Vogelsang, Thiemo Alexander Faßbach, Paul P. Kossmann, Andreas Vorholt
The synthesis of highly branched long chain amines in one step is still a challenge. The palladium catalysed telomerisation of the renewable sesquiterpene farnesene with secondary amines gives a new reaction pathway, which was investigated. Preliminary, a suitable palladium catalyst system was developed by a high-throughput screening. It efficiently allows for the synthesis of tertiary amines with a highly branched C30-carbon chain. A yield of 94% for the desired allylic C30-amines was achieved. The scope of feasible amines was expanded to thirteen amines with linear and branched alkyl and aryl groups. A correlation between the scaffold of the amine, basicity and the activity as nucleophile in the telomerisation reaction was uncovered. Based on the different polarities of the nonpolar in-situ formed C30 substituted amines and the polar solvent, a proof of concept for catalyst recovery by simple decantation was shown.
Surface-improved asymmetric Michael addition catalyzed by amino acids adsorbed on laponite Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-07 György Szőllősi, Dániel Gombkötő, Attila Mogyorós, Ferenc Fülöp
An unprecedented enantioselectivity increase was observed in the presence of inorganic oxides in the asymmetric Michael addition of aldehydes to trans-β-nitrostyrene derivatives catalyzed by amino acids. The best results were reached in the L-proline catalyzed addition of linear aldehydes using laponite RD as additive, approaching those obtained using synthetic chiral organocatalysts. In our study we have shown that the asymmetric Michael addition is catalyzed by the organic-inorganic hybrid material formed in situ by adsorption of the amino acid on the solid surface. The chiral solid catalyst could be pre-prepared and recycled several times with maintained stereoselectivities, showing a slow decrease in the activity, which could be restored by adding proline during reuse. Characterization of the chiral hybrid material by FT-IR spectroscopy and XRD measurements indicated anchoring of the proline on the surface of the laponite particles. Effect of the chiral organocatalyst structure was used to evidence the involvement of both the carboxylic acid and the amino group in anchoring the organic compound on the solid surface. Linear natural amino acids became also active in the asymmetric Michael addition following adsorption on laponite and provided the opposite enantiomer in excess as compared with L-proline. The heterogeneous catalyst was applied in reactions of various carbonyl compounds and substituted nitrostyrene derivatives. Based on results obtained in this study combined with the previously reported amino acid catalyzed reactions on solid surfaces and the recently revisited reaction mechanism of this asymmetric addition a plausible reaction pathway occurring on the surface was proposed.
Chemoselective synthesis of N-arylbenzamides and benzoyloxyacetanilides from aryl isocyanides: Styrene as aryl and arylcarboxymethylene source Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-07 Poonam Sharma, Nidhi Jain
Styrenes serve as a unique aryl or arylcarboxymethylene source towards aryl isocyanides in presence of Cu(II)/TBHP, and yield N-arylbenzamides or benzoyloxyacetanilides respectively. The chemoselectivity of the reaction is controlled by the nature of the substituents present on styrene ring. While styrenes substituted with electron-releasing alkyl and alkoxy groups yield N-arylbenzamides; unsubstituted styrene and those with electron withdrawing substituents furnish benzoyloxyacetanilides as the major product. With benzylamines as substrate, N-arylbenzamides are formed exclusively as they act only as an aryl donor. TBHP serves as a promoter and oxygen source. Both the pathways are believed to proceed through an initial oxidative C−C bond cleavage of styrene.
Organocatalytic Enantioselective aza-Friedel-Crafts Reactions of Pyrazolinone Ketimines with Hydroxyindoles and Electron-Rich Phenols Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-05 Zhong-Tao Yang, Wu-Lin Yang, Long Chen, Hao Sun, Wei-Ping Deng
A variety of enantioenriched indole derivatives substituted in the benzene ring were synthesised via an organocatalytic asymmetric aza-Friedel-Crafts reaction of pyrazolinone ketimines with hydroxyindoles. This reaction was also applicabled to electron-rich phenols, yielding the desired products in high yields (up to 99%) and excellent stereo-selectivities (91-99% ee). Moreover, this method presents its potential in the synthesis of structurally novel indole-pyrazolinone conjugate derivatives.
Catalyst-Free One-Pot Access to Pyrazoles and Disulfide-Tethered Pyrazoles via Deamidative Heteroannulation of β-Ketodithioesters with Semicarbazide Hydrochloride in Water Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-05 MAYA SINGH, Suvajit Koley, Sumit Kumar Panja, Sonam Soni
An operationally simple, mild, and catalyst-free one-pot protocol to access privileged pyrazoles and disulfide-tethered pyrazoles has been devised by [3 + 2] heteroannulation of β-ketodithioesters with semicarbazide hydrochloride in water under open air. The pH of the medium played a key role toward the selectivity switch, as refluxing in water led to the formation of pyrazoles, whereas addition of sodium acetate in water enabled the formation of disulfide-tethered pyrazoles. Notably, this protocol involves a tandem sequence of amination/cyclization/dehydration/hydrodesufurization/hydrolysis/deamidative reactions. A mechanistic rationale for this regio-/chemoselective domino reaction is outlined, which is well supported and validated by density functional theory calculations.
Nickel-Catalyzed Tandem Knoevenagel Condensation and Intramolecular Direct Arylation: Synthesis of Pyrazolo[5,1-a]isoquinoline Derivatives Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-05 Shiv Dhiman, Nitesh Nandwana, Dalip Kumar, Hitesh K Saini, Krishnan Rangan, Mukund Jha, Katherine N Robertson, Anil Kumar
Abstract. A simple and efficient method for the synthesis of pyrazolo[5,1-a]isoquinoline derivatives has been developed using the nickel-catalyzed reaction of 1-aryl-2-(1H-pyrazol-1-yl)ethan-1-ones and 2-bromobenzaldehydes. The overall transformation involves tandem Knoevenagel condensation and intramolecular direct arylation via activation of the C5‒H bond of the pyrazole ring. A series of twenty seven drug-like aroyl‒substituted pyrazolo[5,1-a]isoquinolines have been synthesized in moderate to good yields.
Chiral Ion-pair Organocatalyst Promoted Efficient Enantio-selective Reduction of α-Hydroxy Ketones Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-05 Yiliang Zhang, Li He, Lei Shi
Abstract. The enantioselective reduction of α-hydroxy ketones with catecholborane has been developed employing 5 mol% of a BINOL-derived ion-pair organocatalyst. This methodology provides a straightforward access to the corresponding aromatic 1,2-diols in high yields (up to 90%) with excellent enantioselectivities (up to 97%). Furthermore, the α-amino ketones also could be reduced with moderate ee values under mild reaction condition.
Base-Promoted Carbonylative Cyclization of Propargylic Amines with Selenium under CO gas-free Conditions Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-02 Xiao-Feng Wu, Ming lai, hai wang, jin-bao peng, xinxin qi, jun Ying
We report here a new carbonylative procedure for the cyclization of propargylic amines with elemental selenium (Se). By using tBuOK as the promoter, various 1,3-selenazolidin-2-ones were produced without the usage of toxic CO gas. Benzene-1,3,5-triyl triformate (TFBen) was employed as a safe and convenient CO surrogate here, and a broad class of substrates (29 examples) were effectively transformed into the desired products in 50-97% yields under mild conditions.
A Palladium NNC-Pincer Complex as an Extremely Efficient Catalyst Precursor for the Mizoroki–Heck Reaction Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-02 Go Hamasaka, Shun Ichii, Yasuhiro Uozumi
The Mizoroki–Heck reaction of aryl halides (iodides, bromides, or chlorides) with activated alkenes in the presence of a palladium NNC-pincer complex at ppb to ppm loadings gave the corresponding internal alkenes in excellent yields. The total turnover number and turnover frequency reached up to 8.70 × 108 and 1.21 × 107 h–1 (3.36 × 103 s–1), respectively. The catalyst was applied in a ten-gram-scale synthesis of the UV-B sunscreen agent octinoxate (2-ethylhexyl 4-methoxycinnamate). Reaction-rate analyses, transmission electron microscopic examination of the reaction mixture, and poisoning tests suggested that a monomeric palladium species is the catalytically active species in the catalytic cycle.
A Versatile Reagent and Method for Direct Aliphatic Sulfonylation Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-01 Andre Shavnya, Kevin D. Hesp, Andy S. Tsai
An efficient methodology has been developed for the two-step synthesis of aliphatic sulfinate salts, sulfonamides, sulfonyl fluorides, and unsymmetrical sulfones on the basis of alkylation of a new versatile sulfonylating reagent. The new reagent is easily accessible; the developed protocols are conducted under mild conditions and have a broad substrate scope.
Base-Catalyzed Cascade Reaction of ortho-(Propargylamino)aryl Ketones with N-, O-, or S-Based Nucleophiles for the Synthesis of 3-Functionalized Quinoline Scaffolds Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-03-01 Min Shi, Liu-Zhu Yu, Hao-Zhao Wei
A metal-free and base-catalyzed cascade reaction of ortho-(propargylamino)aryl ketones with primary alcohols, secondary amines including various N-heterocycles and thiols through 1,4-benzoxazepine intermediates was developed, providing a series of synthetically and medically valuable 3-functionalized quinoline derivatives. The reaction process was easily manipulable and environmentally benign, producing 1.0 equiv of water as the sole byproduct. Furthermore, bimolecular reactions for the synthesis of products containing two quinoline units were also achieved utilizing this newly developed protocol.
Organocatalytic Enantioselective Friedel–Crafts Alkylation/Lactonization Reaction of Hydroxyindoles with Methyleneoxindoles Adv. Synth. Catal. (IF 5.646) Pub Date : 2017-12-13 Mengjie Xiao, Dengfeng Xu, Weihong Liang, Wenyu Wu, Albert S. C. Chan, Junling Zhao
Metal-Free Multicomponent Reaction for Synthesis of 4,5-Disubstituted 1,2,3-(NH)-Triazoles Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-28 guanglong wu, Qinpei Wu
A metal-free domino reaction was developed for efficient synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles by sequentially coupling sulfur salts with aldehydes and sodium azide. In the presence of L-proline, olefinic sulfur salt intermediates rather than epoxides are in situ formed via the coupling of sulfur salts with aldehydes and cyclize with azide ion. This process features mild conditions, high efficiency, commercially starting materials, and wide substrate scopes.
Halogen-Bond-Promoted α-C-H Amination of Ethers for the Synthesis of Hemiaminal Ethers Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-28 Zhangjin Pan, Zhenwei Fan, Beili Lu, Jiajia Cheng
A simple halogen-bond-promoted α-C-H amination of ether/thioether with a variety of N-H compounds has been accomplished. In the presence of low-cost and readily available perﬂuorobutyl iodide, a diverse range of hemiaminal ether derivatives, including the valuable hydrazone hemiaminal ethers, were quickly assembled under thermo or visible-light irradiation conditions. Mechanistic studies suggest that a halogen-bond adduct was formed and a radical chain pathway might be operative. Synthetic application of the method has been demonstrated via the preparation of anti-viral and anti-tumor drug, Tegafur.
Ni-Catalyzed C–F Bond Functionalization of Unactivated Aryl Fluorides and Corresponding Coupling with Oxazoles Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-28 Youzhi Yin, Xiaoyu Yue, Qi Zhong, Hanmin Jiang, Ruopeng Bai, Yu Lan, Hua Zhang
A Ni-catalyzed C–F bond functionalization of unactivated aryl fluorides with oxazoles as coupling partners was developed. Various arylated oxazoles could be obtained in moderate to good yields in the presence of Ni(cod)2/IMes catalytic system. A rapid synthesis of natural product texaline was also demonstrated using this protocol. This transformation could be potentially utilized in regioselective introduction of an oxazole group in late-stage synthetic applications.
Selective Synthesis of Primary Amines from Nitriles under Hydrogenation Conditions Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-27 Masayoshi Yoshimura, Akira Komatsu, Masaru Niimura, Yukio Takagi, Tohru Takahashi, Shun Ueda, Tomohiro Ichikawa, Yutaka Kobayashi, Hiroki Okami, Tomohiro Hattori, Yoshinari Sawama, Yasunari Monguchi, Hironao Sajiki
The hydrogenation of aliphatic nitriles over Pd/C, Pd/Al2O3, and Pd-Au/Al2O3 catalysts were evaluated for the selective hydrogenation of aliphatic nitriles to the corresponding primary amines. The highest selectivity (>99%) toward primary amines was achieved when the reaction was carried out in acetic acid using 10 mol% of 25% Pd-5% Au/Al2O3 under relatively low hydrogen pressure (0.8 MPa). Characterization of the catalysts by XRD, CO adsorption experiments, and EXAFS revealed that the excellent selectivity of 25% Pd-5% Au/Al2O3 toward the synthesis of primary amines is determined by the electronic properties and/or the surface structure resulting from alloying Pd with Au.
Gold-catalyzed Cycloisomerization of 2-Aryl-2-(arylamino)-3-butyn-1-ols toward 2-(2'-Aminoaryl)-2,5-dihydrofurans Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-27 Jianlin Yang, Yuanhua Wu, Ming Zhang, Dunru Zhu, Ruwei Shen
An interesting and highly selective gold-catalyzed cycloisomerization of 2-aryl-2-(arylamino)-3-butyn-1-ols to afford 2-(2'-aminoaryl)-2,5-dihydrofurans has been reported. The reaction is atom economic and highly efficient, and tolerates many functional groups including the cyano and allyl groups. A plausible mechanism for this new cycloismerization is also proposed.
Sequential Photoredox Catalysis for Cascade Aerobic Decarboxylative Povarov and Oxidative Dehydrogenation Reactions of N-Aryl α-Amino Acids Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-27 Tianju Shao, Yanli Yin, Richmond Lee, Xiaowei Zhao, Guobi Chai, Zhiyong Jiang
A visible-light-driven sequential photoredox catalysis to allow N-aryl α-amino acids to experience efficient cascade aerobic decarboxylative Povarov and oxidative dehydrogenation (ODH) reactions is described. With a dicyanopyrazine-derived chromophore (DPZ) as a photoredox catalyst in both transformations, two series of valuable azaarenes, i.e., 4-amino tetrahydroquinolines (THQs) and quinolines, were obtained in satisfactory yields featuring diverse 2- and 2,3-substituent patterns. To enable the ODH reaction of 4-amino THQs, a cooperative catalysis with N-hydroxyphthalimide was developed. Additionally, an unprecedented synthesis of chiral N-amino-2-methyl THQs with high enantioselectivities was realized.
Synthesis, Application and Kinetic Studies of Chiral Phosphite-Oxazoline Palladium Complexes as Active and Selective Catalysts in Intermolecular Heck Reactions Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-27 Zahra Mazloomi, Marc Magre, Efrem del Valle, Miquel Àngel Pericàs, Oscar Pàmies, Piet van Leeuwen, Montserrat Diéguez
This study identifies new phosphite-oxazoline ligands that have been successfully applied in the palladium-catalyzed intermolecular asymmetric Heck reaction. The design of the new phosphite-oxazoline ligands derives from a previous successful generation of phosphine-oxazoline ligands, by replacing the phosphine group with several π-acceptor biaryl phosphite moieties. With these simple modifications, the new phosphite-based ligands, unlike previous phosphine-oxazoline, not only present a modular design with numerous potential phosphite groups available, but they are also air-stable solids, which can be made in the same number of synthetic steps as the phosphine analogues. The substitution of the phosphine by a biaryl phosphite group extended the range of substrates and triflates sources that can be coupled with regio-, enantioselectivities and activities comparable to the few best ones reported. In addition, the ligands that provided the best selectivities contained an isopropyl oxazoline moiety instead of the tert-butyl group found in the related phosphine-oxazoline ligands, which is made from a much more expensive precursor. In this paper we have also carried out kinetic studies and a Hammett plot analysis to determine the rate determining step of this system in the regime of interest. We suggest a likely explanation for the fast Heck reaction of the phosphite-oxazoline catalysts.
Water-Soluble Sulfo-Fluorous Affinity (SOFA) Tag-Assisted Enzymatic Synthesis of Oligosaccharides Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-26 Kai-Ling Hou, Pei-Yun Chiang, Chien-Hung Lin, Ben-Yuan Li, Wei-Ting Chien, Yu-Ting Huang, Ching-Ching Yu, Chun-Cheng Lin
Herein, we report a bifunctional sulfo-fluorous affinity (SOFA) tag-assisted enzymatic synthesis and purification strategy for the facile preparation of bioactive glycans using fluorous solid-phase extraction (FSPE). The incorporation of a sulfonate moiety onto the heavy fluorous tag significantly increases its water solubility, which allows the broad use of the inherently hydrophobic fluorous tag in aqueous buffers. In addition, the SOFA tag contains a photocleavable linker, enabling the easy release of amino-functionalized oligosaccharides by UV irradiation. The SOFA tag was used in the synthesis of both negatively charged and neutral glycans to demonstrate its broad utility as an acceptor toward six different glycosyltransferases, significantly improving the feasibility of the preparation of complex glycans using FSPE. All the reactions were performed in an aqueous buffer, a minimum amount of methanol was used to purify the products, and the SOFA tag was easily recovered after photo-irradiation. Thus, the entire synthetic process is environmentally benign.
Cu(I)-Catalyzed Site Selective Acyloxylation of Indoline Using O2 as the Sole Oxidant Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-22 Ashfaq Ahmad, Himangsu Sekhar Dutta, Bhutttu Khan, Ruchir Kant, Dipankar Koley
A Cu(I)-catalyzed regioselective cross-dehydrogenative coupling of indoline with a variety aryl and alkyl carboxylic acids is described. The divergent process for the oxygenation was achieved in satisfactory yields under additive free conditions, which provides an efficient strategy for the regioselective C7 functionalization of indolines using inexpensive copper catalyst. Oxygen as the sole oxidant is required in this protocol. The method is tolerated by a wide range of functional groups. Preliminary mechanistic study provided support for a reversible C–H bond metallation step.
Conjugate Additions of Amines to Maleimides via Cooperative Catalysis Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-22 Karl Scheidt, Brice Uno, Kristine Deibler, Carlos Villa, Arjun Raghuraman
A cooperative system comprising of a lithium Lewis acid and amine base significantly enhances the rate of the conjugate addition of a wide array of amines to maleimides. This operationally simple, scalable method provides mono-addition products in high yields and purity. This conjugation was successfully applied to the kinase inhibitor crizotinib in a chemoselective fashion to create novel fluorescent probes.
Naphthalenediimide – A Unique Motif in Macrocyclic and Interlocked Supramolecular Structures Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-22 Andreea Diac, Mihaela Matache, Ion Grosu, Niculina D. Hădade
Aqueous α-arylation of mono- and diarylethanone enolates at low catalyst loading Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-21 Iratxe Astarloa, Raul SanMartin, María Teresa, Esther Domínguez
Acetophenone and deoxybenzoin derivatives are selectively α-arylated using a combination of very small amounts of palladium acetate and diphenylphosphine oxide as catalyst system and water as the only solvent. Target di- and triarylethanones are isolated virtually free of metal residues, and the reaction is amenable to gram-scale. A mechanistic proposal based on TEM images, poisoning experiments, kinetic plot and ESI-MS spectrometry is also provided.
Synthesis of Spirofurooxindoles via Phenyliodine(III) Bis(trifluoroacetate) (PIFA)-Mediated Cascade Oxidative C–O and C–C Bond Formation Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-21 Desong Sun, Xiaoyuan Zhao, Bobo Zhang, Ying Cong, Xintong Wan, Mingmai Bao, Xue Zhao, Bing Li, Daisy Zhang-Negrerie, Yunfei Du
Upon treatment with solely a hypervalent iodine reagent of phenyliodine(III) bis(trifluoroacetate) (PIFA), 3-(2-hydroxyphenyl)-3-oxo-N-phenyl propanamides and a series of its derivatives were conveniently converted to a class of undocumented spirofurooxindolesunder mild conditions. Control experiments provided evidence that this spirocyclization process encompassed a cascade oxidative reactions involving the formation of a C–O bond prior to that of C–C bond.
Regioselective Silver-Catalyzed Carbon-Phosphorus Difunctionalization of Maleimides: One-Step Construction of Phosphonylated Indolylmaleimides and Pyrrolylmaleimides Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-21 Zhen-Hua Yang, Hong-Ru Tan, Jia-Nan Zhu, Jian Zheng, Sheng-Yin Zhao
An efficient silver-catalyzed intermolecular carbon-phosphorus difunctionalization of maleimides with indoles/pyrroles and organophosphorus compounds including dialkyl phosphites and diphenylphosphine oxide was developed. A diverse range of phosphonylated indolylmaleimides and pyrrolylmaleimides were obtained in good yields with excellent regioselectivity, involving C−P and C−C bond formations. This methodology is very practical and features one-step construction of difunctionalized maleimides.
Intermolecular electrochemical C(sp3)-H/N-H cross-coupling of xanthenes with N-alkoxyamides: radical pathway mediated by ferrocene as a redox catalyst Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-20 mengying lin, kun Xu, yangye jiang, yongguo liu, baoguo sun, Cheng-Chu Zeng
Efficient intermolecular cross dehydrogenative coupling of N-alkyloxyamides with xanthenes is reported. The protocol was proceeded in an undivided cell under constant current conditions employing simple, cheap and readily available ferrocene (Fc) as the redox catalyst. Cyclic voltammetry and control experiments disclosed that the cross dehydrogenative coupling reaction may proceed via an amidyl radical. This work represents the first example of intermolecular electrochemical C(sp3)-H/N-H cross dehydrogenative coupling using a redox mediator.
Iron-Catalyzed Ring-Opening/Allylation of Cyclobutanone Oxime Esters with Allylic Sulfones Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-18 Li-Na Guo, Jing-Feng Zhao, Pin Gao, Xin-Hua Duan
An iron-catalyzed radical allylation of cyclo-butanone oxime esters with allylic sulfones via C−C bond cleavage is reported. This protocol provides a straightforward approach to cyanoalkylated alkenes with good functional group tolerance and high regioselectivity. Furthermore, this reaction can be further expanded to ring-opening of less-strained cyclopentanone oxime esters, leading to desired cyanoalkylated alkenes in good yields.
Aniline ortho C-H Sulfuration/Cyclization with Elemental Sulfur for Efficient Synthesis of 2-Substituted Benzothiazoles under Metal-Free Conditions Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-17 Guojun Deng, Jingjing Jiang, Guozheng Li, Feng Zhang, Hao Xie
A three-component synthesis of 2-substituted benzothiazoles from aryl amines, elemental sulfur and styrenes or aryl acetylenes in 1-methylpyrrolidin-2-one (NMP) is described. Two C-S and one C-N bonds were selectively formed in one-pot under metal-free conditions.
Chemoenzymatic Approaches to the Synthesis of the Calcimimetic Agent Cinacalcet Employing Transaminases and Ketoreductases Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-17 Lisa Marx, Nicolás Ríos-Lombardía, Judith Farnberger, Wolfgang Kroutil, Ana Isabel Benítez-Mateos, Fernando López-Gallego, Francisco Morís, Javier Gonzalez-Sabin, Per Berglund
Several chemoenzymatic routes have been explored for the preparation of cinacalcet, a calcimimetic agent. Transaminases (TAs) and ketoreductases (KREDs) turned out to be useful biocatalysts for the preparation of key optically active precursors. Thus, the asymmetric amination of 1-acetonaphthone yielded an enantiopure (R)-amine, which can be alkylated in one step to yield cinacalcet. Alternatively, the bioreduction of the same ketone resulted in an enantiopure (S)-alcohol, which was easily converted into the previous (R)-amine. In addition, the reduction was efficiently performed with the KRED and its cofactor co-immobilized on the same porous surface. This self-sufficient heterogeneous biocatalyst presented an accumulated total turnover number (TTN) for the cofactor of 675 after 5 consecutive operational cycles. Finally, in a preparative scale synthesis the TA-based approach was performed in aqueous medium and led to enantiopure cinacalcet in two steps and 50% overall yield.
A Tunable Route to Prepare ɑ,β-Unsaturated Esters and ɑ,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-16 Hong-Yan Bi, Feng-Ping Liu, Cui Liang, Gui-Fa Su, Dong-Liang Mo
A tunable strategy to prepare ɑ,β-unsaturated esters and ɑ,β-unsaturated-γ-keto esters in good to excellent yields was developed through copper-catalyzed oxidative coupling of phosphorus ylides with alkenyl boronic acids under mild conditions. The reaction without water afforded ɑ,β-unsaturated esters, ketones, and amides while ɑ,β-unsaturated-γ-keto esters, 1,4-ɑ,β-unsaturated diketones and ɑ,β-unsaturated-γ-keto amides were obtained when using 5.0 equiv. of water. H2O18 labeling experiments showed that water played an important role in the formation of ɑ,β-unsaturated-γ-keto esters. A plausible formation mechanism for ɑ,β-unsaturated esters and ɑ,β-unsaturated-γ-keto esters was proposed based on mechanistic studies. Phosphonium salts could also be used directly as coupling partners instead of phosphorus ylides. The reaction exhibited a broad substrate scope, good functional group tolerance, good regioselectivity, and diverse coupling products.
N-Heterocyclic carbene-catalyzed double Michael addition: stereoselective synthesis of spirofluorenes and multisubstituted indanes Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-16 Fen Xing, Ze-Nan Feng, Ying Wang, Guang-Fen Du, Cheng-zhi Gu, Bin Dai, Lin He
The strong Brønsted basic character of N-heterocyclic carbenes (NHCs) has been used to promote the cascade double Michael addition between fluorenes and dienones. Under catalyst loadings of 1-5 mol% of NHC, fluorene reacts with divinyl ketones (DVKs) to afford anti-spirofluorene compounds in high yields. However, when benzenedi(enones) were employed as Michael acceptors in the presence of 10 mol% of NHC, fluorene undergoes a different inter- and intramolecular cascade double Michael addition providing multi-substituted indanes in high yields with excellent diastereoselectivity.
Manganese(III)-Mediated and -Catalyzed Decarboxylative Hydroxysulfonylation of Arylpropiolic Acids with Sodium Sulfinates in Water Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-16 Yan-Shi Xiong, Jiang Weng, Gui Lu
With water as both solvent and reactant, a novel manganese(III)-mediated and -catalyzed synthesis of β-ketosulfones through decarboxylative hydroxysulfonylation reactions of arylpropiolic acids with sodium sulfinates is described. This protocol has the advantages of mild reaction conditions, short reaction time, easy to handle reagents, purification simplicity, and being environmentally benign, which demonstrate the practical utility of this methodology.
Selenolate Anion as an Organocatalyst: Reactions and Mechanistic Studies Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-15 Oleksandra Trofymchuk, Zhipeng Zheng, Takashi Kurogi, Daniel Mindiola, Patrick J. Walsh
Abstract. A new organocatalyst, the selenolate anion [RSe]–, generated from bench stable and commercially available diphenyl diselenide or from phenyl benzyl selenide (10 mol%) is introduced. Benchmarking is performed in the conversion of benzylic chlorides into trans-stilbenes selectively at room temperature. Mechanistic studies support the intermediacy of the selenolate anion and of 1,2-diphenylethyl phenyl selenide.
Construction of Isoxazolidin-5-ones with a Tetrasubstituted Carbon Center: Enantioselective Conjugate Addition Mediated by Phase-Transfer Catalysis Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-15 Timothée Cadart, Vincent Levacher, Stephane Perrio, jean-François Brière
An efficient enantioselective Michael reaction of readily available α-substituted N-Boc isoxazolidin-5-ones is described under phase transfer conditions with up to 95:5 er. The organocatalytic process is promoted by a low catalytic loading of a commercially available N-spiro quaternary ammonium salt. This sequence opens an entry to chiral heterocyclic platforms displaying a β-amino carbonyl motif with an α-all-carbon quaternary stereogenic center. The methodology was also successfully extended to the asymmetric amination reaction using an azodicarboxylate electrophile.
Nonenzymatic Dynamic Kinetic Resolution of in situ Generated Hemithioacetals: Access to 1,3-Disubstituted Phthalans Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-15 Subhas Pan, Utpal Nath, Deepan Chowdhury
The first nonenzymatic DKR reaction of hemithioacetals is developed. Hemithioacetals were formed in situ via thiol addition and subsequently underwent an intramolecular oxa-Michael reaction. The scope of the reaction was quite broad ranging from aliphatic to aromatic substituents and 1,3-disubstituted-1,3-dihyroisobenzofuran products were obtained in good yields with high diastereo- and enantioselectivities.
Lewis acid-mediated defluorinative [3+2] cycloaddition/aromatization cascade of 2,2-difluoroethanol systems with nitriles Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-15 Min-tsang Hsieh, Kuo-Hsiung Lee, Sheng-Chu Kuo, Hui-Chang Lin
The properties of C-F bonds, including high thermal and chemical stability, make derivatization of organic fluorine-containing compounds by the activation of the C-F bond and subsequent functionalization quite challenging. We herein report a Lewis acid-mediated defluorinative cycloaddition/aromatization cascade of 2,2-difluoroethanols with nitriles as a novel synthetic method for the preparation of 2,4,5-trisubstituted oxazoles. This reaction, which involves cleavage of two C-F bonds and the consecutive formation of C-O and C-N bonds in a one-pot fashion, features a broad substrate scope and moderate to high reaction yields. Mechanistic studies revealed that the reaction is initiated by the Lewis acid-mediated ring closure of the 2,2-difluoroethanol to produce the fluoroepoxide intermediate.
A three-component cascade cyclization to construct 3-(2-oxopropyl)-2-arylisoindolinone derivatives via copper-catalyzed annulation Adv. Synth. Catal. (IF 5.646) Pub Date : 2018-02-15 li liu, Shu-Hua Bai, Yang Li, Xiao-Dan Ding, Qian Liu, Jian Li
An efficient synthesis of a variety of poly-substituted isoindolinone derivatives via Cu-catalyzed three-component cascade cyclization among 2-formylbenzonitriles, alkyl aryl ketones/prop-1-en-2-ylbenzene and diaryliodonium salts is achieved. Various isoindolinone derivatives could be obtained in good to excellent yields. A concise synthesis of dihydroisoindolo[2,1-a]quinolin-11(5H)-ones have been achieved using this method.
Photocatalytic Oxidative Bromination of Electron-Rich Arenes and Heteroarenes by Anthraquinone Adv. Synth. Catal. (IF 5.646) Pub Date : 2017-11-16 Daniel Petzold, Burkhard König
Palladium-Catalyzed Three-Component Tandem Reaction for One-pot Highly Stereoselective Synthesis of (Z)-α-Hydroxymethyl Allylic Sulfones Adv. Synth. Catal. (IF 5.646) Pub Date : 2017-11-06 Yunlei Hou, Qi Shen, Zefei Li, Shaowei Chen, Yanfang Zhao, Mingze Qin, Ping Gong
Copper-Mediated Tandem C(sp2)-H Amination and Annulation of Arenes with 2-Aminopyridines: Synthesis of Pyrido-fused Quinazolinone Derivatives Adv. Synth. Catal. (IF 5.646) Pub Date : 2017-12-12 Jidan Liu, Jinhui Zou, Jiawei Yao, Guoshu Chen
Chiral Phosphoric Acid Catalyzed Enantioselective Friedel-Crafts Reaction of N-Protected 4-Aminoindoles with β,γ-Unsaturated α-Ketimino Esters Adv. Synth. Catal. (IF 5.646) Pub Date : 2017-12-12 Yu-Yang Ding, Deng-Feng Xu, Shan-Shui Meng, Yang Li, Jun-Ling Zhao
Synthesis of Cyclobutene-Fused Eight-Membered Carbocycles through Gold-Catalyzed Intramolecular Enyne [2+2] Cycloaddition Adv. Synth. Catal. (IF 5.646) Pub Date : 2017-12-13 Tomohiro Iwai, Masahiro Ueno, Hiori Okochi, Masaya Sawamura
Hydrogenation of Carbonyl Derivatives Catalysed by Manganese Complexes Bearing Bidentate Pyridinyl-Phosphine Ligands Adv. Synth. Catal. (IF 5.646) Pub Date : 2017-12-14 Duo Wei, Antoine Bruneau-Voisine, Téo Chauvin, Vincent Dorcet, Thierry Roisnel, Dmitry A. Valyaev, Noël Lugan, Jean-Baptiste Sortais
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