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Rhodium(III)-Catalyzed Three-Component Cascade Annulation for Modular Assembly of N-Alkoxylated 3-Arylisoindolin-1-ones with Tetrasubstituted Carbon Center Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-23 Wenbo Hu, Liqin Yan, Youpeng Zuo, Shuwen Kong, Yue Pu, Qiang Tang, Xinyu Wang, Xinwei He, Yongjia Shang
A cascade C-H activation, annulation and etherification protocol of N-hydroxybenzamides with propargylamines provides a flexible and powerful route to N-alkoxylated 3-arylisoindolin-1-ones. Three new bonds (C-C, C-N, and C-O) are generated to afford a series of isoindolin-1-ones bearing a tetrasubstituted carbon in 49% to 82% yields. The utility of this method is showcased by gram-scale synthesis,
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Iron(III)-catalyzed difluoroalkylation of aryl alkynes with difluoroenol silyl ether in the presence of trimethylsilyl chloride Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-22 Meng-Meng Guo, Xuan-Di Song, Xiang Liu, Ya-Wen Zheng, Xue-Qiang Chu, Weidong Rao, Zhi-Liang Shen
The reaction of non-fluorinated silyl enol ether with alkyne is useful for the synthesis of β,γ-unsaturated carbonyl compounds. However, most of the existing methods for realizing such organic transformation usually employ stoichiometric amounts of relatively expensive Lewis acids/metallic salts. Herein, an iron(III)-catalyzed difluoroalkylation of aryl alkynes with difluoroenol silyl ether was developed
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Bromide-catalyzed electrochemical Csp3-H oxidation of acetonitrile: Stereoselective synthesis of heteroaryl vinyl sulfides Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-22 Jin-Lin Wan, Jing-Mei Huang
An electrochemical oxidative C-H/S-H cross-coupling reaction between acetonitrile and heteroaryl thiols has been developed. Me4NBr is employed as a redox catalyst to oxidize both the Csp3-H of acetonitrile and S-H of heteroaryl thiols. Heteroaryl vinyl sulfides were afforded under metal-free and oxidant-free reaction conditions in good yields and stereoselectivities with excellent functional group
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Well-defined [Cp*Co(N,O)I]-Catalysts for Site-selective Intramolecular C-H Amidation Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-22 Pardeep Dahiya, Ankita Sarkar, Basker Sundararaju
We present an efficient method for forming C-N bonds via intramolecular amidation catalyzed by well-defined Cp*Co(N,O)I complexes. The reaction has been operate under mild conditions and produced a regioselective amidation product without the use of a bulky anion or expensive fluorinated solvents. The Cp*Co(N,O)-I catalyst is very effective for intramolecular benzylic, tertiary, and internal C(sp3)-H
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Asymmetric Metal-Templated Route to Amino Acids with 3-Spiropyrrolidine Oxindole Core via a 1,3-Dipolar Addition of Azomethine Ylides to a Chiral Dehydroalanine Ni(II) Complex Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-20 Zalina Gugkaeva, Maria Panova, Alexander Smolyakov, Michael Medvedev, Alan Tsaloev, Ivan Godovikov, Victor I. Maleev, Vladimir Larionov
We herein developed a protocol for the asymmetric synthesis of artificial AAs featuring a 3-spiropyrrolidine oxindole skeletal with continuous tetrasubstituted carbon stereocenters by a 1,3-dipolar cycloaddition reaction of in situ generated azomethine ylides with a chiral dehydroalanine Ni(II) complex. A three-component reaction of the Ni(II) complex with various isatins and AAs in green solvent (ethanol)
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Lewis Acid-Assisted Transition Metal-Free Aminocyanation of Alkynes with Arylamines and N-Cyanosuccinimide Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-17 Indranil Chatterjee, Gautam Kumar, Debkanta Bhattacharya
A transition-metal-free aminocyanation of aryl alkynes has been achieved using indium tribromide, InBr3 or B(C6F5)3 as a Lewis acid. This aminocyanation protocol features with non-toxic cyanide source, a good substrate scope and valuable aminocyanation products. Mechanistic studies reveal the complex formation between Lewis acid and alkyne to produce in situ alkyne nitrile as a key intermediate. Further
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4-(Dimethylamino)pyridinium Azide in Protic Ionic Liquid Media as a Stable Equivalent of Hydrazoic Acid Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-15 Ivan Andreev, Maksim Boichenko, Nina Ratmanova, Olga Ivanova, Irina Levina, Victor Khrustalev, Igor Sedov, Igor Trushkov
We report a procedure for the multigram synthesis of 4-(dimethylamino)pyridinium azide, stable, non-explosive, low-hygroscopic source of azide ion soluble in both protic and aprotic organic solvents. In protic ionic liquid media this reagent was shown to serve as a safer equivalent of toxic and unstable hydrazoic acid. The high synthetic utility of this system was demonstrated using donor-acceptor
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Chichibabin-Type Phosphonylation of 2-(Hetero)aryl Pyridines: Selective Synthesis of 4-Phosphinoyl Pyridines via an Activated N-benzylpyridinium Salt Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-15 Xiao Yang, Rui Sun, Chunchun Zhang, Yan Zhang, Zhishan Su, Yicen Ge, Hua Chen, haiyan Fu, Ruixiang Li
A direct C-H phosphonylation of pyridine by N-benzylating activation is reported, which afforded 4-pyridylphosphine oxides with high regioselectivity, without the employment of metal catalyst or expensive activator. By increasing the electrophilicity of pyridinium with electron-withdrawing substituents on the N-benzyl group, the phosphonylation process could be realized at room temperature. Control
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Mechanochemically Induced Cross Dehydrogenative Coupling Reactions under Ball Milling Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-15 Brindaban Ranu, Ilya Egorov, Anindita Mukherjee, Sougata Santra, Dmitry Kopchuk, Igor Kovalev, Grigory Zyryanov, Adinath Majee, Oleg Chupakhin, Yuanli Liu
Cross dehydrogenative coupling (CDC) reactions have become a convenient synthetic strategy for the synthesis of various (het)aromatic scaffolds. In recent times ball milling (BM) has emerged as a powerful tool to perform reactions in a greener way. The current review highlights various applications of cross dehydrogenative coupling reactions under ball milling towards synthesis of useful molecules
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Ir-Catalyzed Intermolecular Asymmetric Allylic Amination with Pyridones Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-14 Hang-Fei Tu, Yu-Han Nie, Chao Zheng, Shu-Li You
We report herein a catalytic synthetic method for enantioenriched N-substituted pyridones. By employing chiral iridium catalyst generated from the Carreira [P/olefin] ligand, intermolecular asymmetric allylic amination of allyl alcohols with pyridones proceeded smoothly with excellent chemo-, regio- and enantio-selectivities (>19:1 N/O, >19:1 b/l and ≥89% ee). The reaction underwent through a kinetic
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Expanding the Scope of Enantioselective Halohydrin Dehalogenases – Group B Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-13 Emina Mehić, Lucija Hok, Qian Wang, Irena Dokli, Marina Svetec Miklenić, Zvjezdana Findrik Blažević, Lixia Tang, Robert Vianello, Maja Majerić Elenkov
Halohydrin dehalogenases (HHDHs) possess an unnatural activity of introducing functionalities such as N3, CN, NO2 etc., into a molecule through the ring-opening reaction of epoxides. The enantioselectivity of HHDHs is substrate-dependent and not always high enough for synthetic applications. B-group of HHDHs has been neglected in the past, due to observed low enantioselectivity based on performance
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Palladium-Catalyzed Synthesis of Carbazoles by Perester Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-13 Li He, Yongjun Xu
An intramolecular C-H amination for the synthesis of carbazoles with a Pd(II)/ TBPB system has been developed. This catalytic amination process forms the carbazole products in good to excellent yields. It is noteworthy that this method implied the advantages of the catalytic mode involving perester with transition metal catalyst in the activation of inert C-H bonds. In addition, the transformation
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PPh3-Mediated Wittig-like/Mannich Tandem Reactions of 2‑Alkynylnitrobenzenes with Ketones for the Synthesis of 2,2-Disubstituted Indolin-3-ones Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-13 Hui Fan, Yao Xu, Fan Yang, Shijie Xu, Xuechun Zhao, Xiaoxiang Zhang
A synthetic strategy for the construction of 2,2-disubstituted indolin-3-ones from 2-alkynylnitroarenes and ketones has been described. The corresponding indolin-3-one derivatives were afforded in moderate to excellent product yields by using mild conditions. After a Wittig-like process, the key intermediates 3H-indol-3-ones were generated from 2-alkynylnitroarenes, which could be further transformed
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Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic N-Carbamoyl Hydrazones Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-13 Saúl Alberca, Marta Velázquez, José Trujillo, Javier Iglesias, Rosario Fernández, José Lassaletta, David Monge
Catalysts generated by combinations of Pd(TFA)2 and pyridine-hydrazone ligands have been applied to 1,2 addition of arylboronic acids to aliphatic N-carbamoyl (Cbz) hydrazones, affording protected α-aryl monoalkylhydrazines with high enantioselectivities (37-99% ee). Subsequent removal of the benzyloxy carbonyl protecting group provides a direct entry to free monosubstituted hydrazines, key building
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Insight into the Stereocontrol of DNA Polymerase-Catalysed Reaction by Chiral Cobalt Complexes Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-12 Ya Wu, Xinya Bu, Yongqi Ke, Huaming Sun, Jingyao Li, Lu Chen, Wei Cui, Yujian He, Li Wu
Enantiomers of chiral substances typically have distinct biological activities, thus, the explorations of biochemical processes at the enantiomeric level has has very high significance. This study investigated DNA polymerase–catalyzed reaction modulated by various types of chiral cobalt complexes. The experimental data showed that polymerase reactions were inhibited or accelerated in the presence of
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Electrochemical Decarboxylative Coupling of N-Substituted Glycines under Air: Access to C3-Aminomethylated Imidazo[1,2-a]pyridines Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-09 Sifeng Li, Xingchen Li, Taimin Wang, Qingjing Yang, Zijun Ouyang, Jieyu Chen, Hongbin Zhai, Xiao Li, Bin Cheng
An electrochemical decarboxylative aminomethylation reaction of imidazo[1,2-a]pyridines with various N-substituted glycines in acetonitrile at room temperature has been described. The reaction could be conducted under light-free, catalyst-free, oxidant-free, and air conditions, affording the C3-aminomethylated imidazo[1,2-a]pyridines in good to high yields. Remarkably, N-aryl, N,N-dialkyl, and N-alkyl-N-aryl
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Synthesis of Saturated N-Heterocycles via a Catalytic Hydrogenation Cascade Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-08 Tobias Wagener, Marco Pierau, Arne Heusler, Frank Glorius
Saturated N-heterocycles are prominent motifs found in various natural products and pharmaceuticals. Despite the increasing interest in this class of compounds, the synthesis of saturated bicyclic azacycles requires tedious multi-step syntheses. Herein, we present a one-pot protocol for the synthesis of octahydroindoles, decahydroquinolines, and octahydroindolizines through a cascade reaction.
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Aryl-Alcohol-Oxidase-Mediated Synthesis of Piperonal and Other Valuable Aldehydes Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-05 Nina Jankowski, Katja Koschorreck, Vlada B. Urlacher
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Low-Voltage-Driven Electrochemical Aerobic Oxygenation with Flavin Catalysis: Chemoselective Synthesis of Sulfoxides from Sulfides Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-03 Taiga Mizushima, Marina Oka, Yasushi Imada, Hiroki Iida
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Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-03 Muhammad Aliyu Idris, Kwang Ho Song, Sunwoo Lee
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Silver-Catalyzed Asymmetric Aldol Reaction of Isocyanoacetic Acid Derivatives Enabled by Cooperative Participation of Classical and Nonclassical Hydrogen Bonds Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-03 Satoshi Sakai, Akane Fujioka, Koji Imai, Kei Uchiyama, Yohei Shimizu, Kosuke Higashida, Masaya Sawamura
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Regioselective Photocatalytic Dialkylation/Cyclization Sequence of 3-Aza-1,5-dienes: Access to 3,4-Dialkylated 4-Pyrrolin-2-ones Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-02 Xiao Hu, Minglin Tao, Zhongxiao Ma, Yi Zhang, Yanni Li, Deqiang Liang
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Copper-Catalysed Synthesis of Propargyl Alcohol and Derivatives from Acetylene and other Terminal Alkynes Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-02 Nikolai A. Sitte, Francesca Ghiringhelli, Grigory A. Shevchenko, Frank Rominger, A. Stephen K. Hashmi, Thomas Schaub
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Stereocomplementary Synthesis of a Key Intermediate for Tofacitinib via Enzymatic Dynamic Kinetic Resolution-Reductive Amination Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-02 Zhuangzhuang Zhan, Zefei Xu, Shanshan Yu, Jinhui Feng, Fufeng Liu, Peiyuan Yao, Qiaqing Wu, Dunming Zhu
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Visible-Light Photoredox Catalyzed Decarboxylative Alkylation of Vinylcyclopropanes Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-01 Palasetty Chandu, Debabrata Das, Krishna G. Ghosh, Devarajulu Sureshkumar
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Visible-Light-Mediated C-2 Functionalization and Deoxygenative Strategies in Heterocyclic N-Oxides Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-06-01 Jitender Singh, Roshan I. Patel, Anuj Sharma
Heterocyclic N-oxides are prevalent in numerous natural products with broad applications in pharmaceuticals, agrochemicals, material sciences, and asymmetric synthesis. Owing to their profound biological and physiological activity and unique chemical reactivity, the importance of these compounds has stimulated substantial interest among organic synthetic chemists. More importantly, C-2 functionalization
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Synthesis of Tricyclic [1,2-a]Indoles via Nickel-Catalyzed Intramolecular Imine-Alkene Coupling Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-31 Wei-Min Feng, Xian-Ming Liu, Li-Jun Xiao, Qi-Lin Zhou
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Recent Progress in Solid-Phase Total Synthesis of Naturally Occurring Small Peptides Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-31 Hong Yan, Fen-Er Chen
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Visible-Light-Enabled Photosensitizer- and Additive-Free Decarboxylative Coupling Cyclization of Enaminone with N-Arylglycine for 3-Aminoalkyl Chromones Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-30 Zhi-Qiang Zhu, Jia-Yu Hu, Zong-Bo Xie, Juan Tang, Zhang-Gao Le
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Suzuki Coupling of Activated Aryltriazenes for Practical Synthesis of Biaryls from Anilines Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-29 Dongsheng Guo, Weijia Shi, Gang Zou
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Synthesis of Quinolines and 2-Functionalized Quinolines by Difluorocarbene Incorporation Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-26 Ben-Jie Jiang, Song-Lin Zhang
A general method is developed to allow de novo construction of quinolines and C2-functionalized quinolines from ortho-alkenyl anilines in the presence of a difluorocarbene precursor. This method exploits a crucial reactivity of in-situ generation of isocyanides from condensation of primary aniline with difluorocarbene. Subsequent α-addition of isocyanide by neighbouring alkenyl group constructs the
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Formation of N−P(O)−S Bonds from White Phosphorus via a Four-Component Reaction Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-26 Yue Zhang, Yinwei Cao, Yangyang Chi, Shuanghui Chen, Xiangzhe Zeng, Yan Liu, Guo Tang, Yufen Zhao
Functionalization of white phosphorus with disulfides, amines and KOH to phosphoramidodithioates containing both P−N, P−S and P=O bonds via a four-component reaction is presented. It proceeds with high yields and provides an attractive approach for the construction of valuable N−P(O)−S motif using a one-step strategy. The advantages of this newly developed process include a clean reaction profile,
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Ylide-Functionalized Diisopropyl Phosphine (prYPhos): A Ligand for Selective Suzuki-Miyaura Couplings of Aryl Chlorides Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-25 Xiao-Jing Wei, Bingxiang Xue, Jens Handelmann, Zhiyong Hu, Heidar Darmandeh, Viktoria H. Gessner, Lukas J. Gooßen
The ylide-functionalized diisopropyl phosphine (prYPhos) promotes Pd-catalyzed Suzuki-Miyaura couplings of aryl chlorides and bromides with arylboronic acids. Using Pd2(dba)3/prYPhos as the catalyst and K2CO3 as the base, various (hetero)biaryls were synthesized in 45–98% yields at mild reaction conditions, tolerating sensitive functional groups and steric hindrance. The electron rich, sterically demanding
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Well-Defined Ni−SNS Complex Catalysed Borrowing Hydrogenative α-Alkylation of Ketones and Dehydrogenative Synthesis of Quinolines Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-22 Rahul Sharma, Avijit Mondal, Arup Samanta, Nandita Biswas, Babulal Das, Dipankar Srimani
The “borrowing hydrogen” (BH) method for C-alkylation reactions using alcohol as alkylating agents is an important synthetic transformation. In this respect, designing cheap and bench stable earth abundant metal catalyst for borrowing hydrogen transformation is a key challenge to be witnessed. Herein we have presented a synthesis of non-phosphine, easily accessible and bench stable SNS−Ni complexes
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Rhodium(II)-Catalyzed Site-Selective Intramolecular Insertion of Aryldiazoacetates into Unactivated Primary C−H Bond: A Direct Route to 2-Unsubstituted Indanes Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-20 Hisanori Nambu, Ryoya Amano, Takafumi Tamura, Takayuki Yakura
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Visible-Light-Promoted Radical Cyclization and N−N Bond Cleavage Relay of N-Aminopyridinium Ylides for Access to 2,3-Difunctionalized Indoles Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-20 Meng-Meng Xu, Wen-Bin Cao, Xiao-Ping Xu, Shun-Jun Ji
Reported herein is a photocatalytic platform for the vicinal aminopyridylation of indoles. The accurate difunctionalization reaction undergoes a tandem process involving a radical-mediated 1,3-dipolar cycloaddtion which generated from the single-electron oxidation of N-aminopyridinium ylides, a cleavage of the N−N bond as well as an oxidation of indoline ring. The electrophilic pyridyl and nucleophilic
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Direct Thioamination of Cyclohexanones via Difunctionalization with Thiophenol and Aniline Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-19 Minli Tang, Li Zhang, Guojiang Mao, Fuhong Xiao, Wen Shao, Guo-Jun Deng
A synthetic method of o-sulfanylanilines from cyclohexanones, amines, and thiophenols under transition-metal-free conditions is disclosed. This is the first report on the direct thioamination of cyclohexanones via N-iodosuccinimide (NIS) promoted oxidative dehydroaromatization. Non-aromatic cyclohexanones were smoothly dehydrogenated, and acted as an aryl source using oxygen as a green oxidant. The
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Very Important Publication – VIP Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-18 Dean D. Roberts, Mark G. McLaughlin
Organosilicon reagents are highly versatile and privileged scaffolds in modern synthetic chemistry, largely due to the range of transformations the groups are amenable to. The β-Silicon effect is one of the fundamental phenomena underpinning the inherent reactivity of organosilicon reagents, allowing unsaturated organosilanes to undergo a range of electrophilic substitutions with a variety of nucleophiles
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Ruthenium(II)-Catalyzed Hydroamination of Allenoates: A Regioselective Synthesis of Allylamines Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-17 Hua Wang, He Wang, Lei Li, Xin Wang, Ran Sun, Ming-Dong Zhou
A ruthenium(II)-catalyzed hydroamination of allenoates with arylamines has been developed. This strategy provides an approach to synthesize E-allylic amines in good yields with high atom-economy and high levels of chemo-, regio- and E-selectivities with a broad substrate scope.
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Intramolecular Aerobic Ring Expansion of Cyclic Ketone: A Mild Method for the Synthesis of Medium-Sized Lactones and Macrolactones Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-17 Qi-Ming Liang, Jing-Yun Zheng, Si-Yuan Lu, Hong-Mei Wang, Lu Luo, Xiang-Zhi Zhang, Jin-Bao Peng, Na Feng, Ai-Jun Ma
An operationally simple protocol for the synthesis of medium-sized lactones and macrolactones via an intramolecular ring expansion of cyclic ketones has been developed. Using this method, a series of 10- and 12-membered lactones was synthesized under mild conditions. Preliminary mechanistic studies showed that a radical pathway might be involved in this reaction.
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Acidic Hydrogen-Tethered Allylic Carbonates for Phosphine-Catalyzed (4+2) Annulation of Sulfamate-Derived Cyclic Imines Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-16 Min Liu, Jianning Liao, Yujie Dong, Wangyu Shi, Yimin Hu, Jiaqing Xu, Wei Wang, Yong Xu, Hongchao Guo
The acidic hydrogen-tethered allylic carbonates were successfully applied in phosphine catalysis. Their (4+2) annulation reaction with sulfamate-derived cyclic imines under phosphine catalysis worked well to produce tetrahydropyridine-fused heterocyclic compounds in high yields. A moderate ee was obtained in the initial screening. The zwitterionic intermediate produced through in-situ deprotonation
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Direct Asymmetric Addition of Heteroatom Nucleophiles to Imines Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-13 Ilya N. Egorov, Sougata Santra, Grigory V. Zyryanov, Adinath Majee, Alakananda Hajra, Oleg N. Chupakhin
The direct asymmetric addition of heteroatom nucleophiles to imines represents one of the most efficient tools for the formation of carbon-heteroatom bonds and has received much interest recently. The review is devoted to the asymmetric addition reactions of non-carbon nucleophiles to imines. The present review is divided into five main sections: reactions with N-nucleophiles; reactions with P-nucleophiles;
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Photo-Catalyzed Redox-Neutral 1,2-Dialkylation of Alkenes Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-13 Wen-Hui Sun, Jian-Yu Zou, Xiao-Jing Xu, Jin-Lin Wang, Mei-Ling Liu, Xue-Yuan Liu
Difunctionalization of alkenes enables construction of complex compounds in one pot. In this report, we presented an intermolecular, redox-neutral three-component dicarbofunctionalization of activated alkenes under mild reaction conditions. The mechanistic studies indicated tertiary alkyl radicals from oxalate salts were first added to alkenes in Giese-type fashion, followed by nucleophilic addition
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Access to 5-Substituted 3-Aminofuran/Thiophene-2-Carboxylates from Bifunctional Alkynenitriles Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-12 Chandresh Kumari, Avijit Goswami
An atom-economical approach for the synthesis of 3-aminofurans/thiophenes via a conjugate addition of alcohols and thiols with electron withdrawing groups (EWGs) at α positions on alkynenitriles followed by a modified Thorpe-Ziegler cyclization have been reported. This operationally simple protocol offers a rapid access to a library of 3-aminofurans/thiophenes in moderate to good yields.
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Transition Metal-Free Radical α-Oxy C−H Cyclobutylation via Photoinduced Hydrogen Atom Transfer Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-12 Han Gao, Lin Guo, Chengcheng Shi, Yining Zhu, Chao Yang, Wujiong Xia
A transition-metal-free photoinduced radical-mediated α-oxy C−H cyclobutylation reaction of bicyclo[1.1.0]butane (BCB) compounds was described. In this protocol, α-oxy C(sp3)−H motifs including ethers and alcohols were activated via photocatalytic conditions, releasing the ring strain of BCBs and generating 1,3-disubstituted cyclobutanes in 40–80% yields. Control experiments and Stern-Volmer quenching
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Catalyst-Free Visible Light Mediated Synthesis of Unsymmetrical Tertiary Arylphosphines Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-12 Dmitry I. Bugaenko, Alexander V. Karchava
Arylation of tertiary aryl and alkyl phosphines bearing 2-cyanoethyl group with aryl(mesityl)iodonium triflates under blue light irradiation followed by retro-Michael reaction of the in situ generated quaternary phosphonium salts initiated by DBU represent a novel efficient and general method for the preparation of distinctly substituted tertiary arylphosphines. An operationally simple, one-pot protocol
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Visible-Light-Induced [2+2+1] Dearomative Cascade Cyclization of Indole/Furan Alkynes to Synthesize Sulfonyl Polycycles Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-12 Jiajun Luo, Guohui Zeng, Xiaohui Cao, Biaolin Yin
Herein, we report a visible-light-induced [2+2+1] dearomative cascade cyclization of indole/furan alkynes with NaHSO3, providing an array of diverse highly strained sulfonyl polycycles. Compared to our previous work, this method does not require the use of additional sacrificial oxidants and have wider reaction scope. Preliminary mechanistic studies suggest that the indole moiety initiated the reaction
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Substrate-Induced Synthesis of Coumarin-Fused Quinolinones from Anilines, 4-Hydroxycoumarins and DMSO under Air Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-11 Xu Shi, Qingqing Zhang, Anan Wang, Tao-Shan Jiang
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Metal- and Solvent-Free Synthesis of Maleimide Fused Carbazoles from (Indol-3-Yl)cyclohexanones and Maleimides Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-11 Fang Fang, Haolin Zheng, Weipeng Li, Guojiang Mao, Shanping Chen, Guo-Jun Deng
A metal- and solvent-free strategy for the preparation of maleimide-fused carbazoles has been developed. This protocol started from 2-(indol-3-yl)cyclohexanones and maleimides, providing various maleimide-fused carbazoles in 45–90% yields. The present approach was catalyzed by trimethylsulfoxonium iodide and involved a cascade of oxidation, [4+2] annulation, and dehydrogenative aromatization. Moreover
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Substrate-Controlled Regioselectivity Switch in a Three-Component 1,3-Dipolar Cycloaddition Reaction to Access 3,3′-Pyrrolidinyl-Spirooxindoles Derivatives Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-11 Kai-Kai Wang, Yan-Li Li, Rong-Xiang Chen, Ai-Li Sun, Zhan-Yong Wang, Ying-Chao Zhao, Ming-Yue Wang, Shi Sheng
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Defluorinative Alkylation of Trifluoromethyl Alkenes with Soft Carbon Nucleophiles Enabled by a Catalytic Amount of Base Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-11 Ya Gao, Wei Qin, Ming-Qing Tian, Xuefei Zhao, Xu-Hong Hu
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Asymmetric Organocatalyzed Friedel–Crafts Reaction of Trihaloacetaldehydes and Phenols Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-10 David Svestka, Jan Otevrel, Pavel Bobal
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Photogenerated Azido Radical Mediated Oxidation: Access to Carbonyl Functionality from Alcohols, Alkylarenes, and Olefins via Organophotoredox Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-10 Maniklal Shee, N. D. Pradeep Singh
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Copper-Catalyzed Chan-Lam Coupling of NH-Diaryl Sulfondiimines Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-10 Yangyang Wang, Tingting Meng, Shuaisong Su, Limin Han, Ning Zhu, Tiezheng Jia
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Pentafluorophenyl Group as Activating Group: Synthesis of α-Deuterio Carboxylic Acid Derivatives via Et3N Catalyzed H/D Exchange Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-10 Mengqi Peng, Hengzhao Li, Zixuan Qin, Junyu Li, Yanhao Sun, Xiaoxu Zhang, Ling Jiang, Hainam Do, Jie An
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N-Hydroxyphthalimide Catalyzed Aerobic Oxidation of Aldehydes under Continuous Flow Conditions Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-09 Bence S. Nagy, C. Oliver Kappe, Sándor B. Ötvös
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Allylic C(sp3)−C(sp3) Bond Formation Through Pd-Catalyzed C(sp3)−H Activation of Alkenes and 1,4-Dienes Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-09 Jacques Muzart
This review highlights the allylic C−H alkylation of alkenes (AAH) with nucleophiles under Pd0 or PdII catalysis and achiral or chiral conditions. The η3-allylpalladium intermediates of these reactions are formed from the cleavage of an allylic hydrogen which becomes a leaving group, like the acetate moiety of allyl acetates during the classical Tsuji-Trost procedure. Most of these cross-dehydrogenative-couplings
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Tartramide Ligands for Copper-Catalyzed N-Arylation at Room Temperature Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-09 Xuerui Ma, Robert P. Davies
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Synergistic Pd/Cu Catalyzed Allylation of Cyclic Ketimine Esters with Vinylethylene Carbonates: Enantioselective Construction of Trisubstituted Allylic 2H-Pyrrole Derivatives. Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-06 M. Ke, Y. Yu, K. Zhang, S. Zuo, Z. Liu, X. Xiao, F. Chen
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Hypertransglycosylating Variants of the GH20 β-N-Acetylhexosaminidase for the Synthesis of Chitooligomers Adv. Synth. Catal. (IF 5.837) Pub Date : 2022-05-06 Zuzana Mészáros, Lucie Petrásková, Natalia Kulik, Helena Pelantová, Pavla Bojarová, Vladimír Křen, Kristýna Slámová