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Diradical Polar Reactivity Induced by Electricity‐Mediated Ground State Triplet Nitrenium Species Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-09 Nakshatra Banerjee, Apoorv Kushwaha, Shiv Dutt, Debarshi Saha, T. J. Dhilip Kumar, Prabal Banerjee
It is extremely rare for reactive intermediates to possess a ground state triplet character. Excited state triplet intermediates are generally accessed by means of photon transfer from a tunable light source or by using any triplet sensitizers. N‐acyl N‐alkoxy nitreniums are an important class of reactive intermediates in the synthetic organic community due to their prolonged lifetime and ground‐state
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One‐Pot Multicomponent Selective Synthesis of 5‐Trifluoromethyl Pyrimidine Derivatives Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-09 Dingyuan Lou, Yuxin Ding, Zhening Jin, Wenkai Huang, Yuan Shi, Changjun Zhang, Yuanyuan Xie
A one‐pot multi‐component reaction strategy for the selective synthesis of 5‐trifluoromethyl pyrimidine derivatives has been established. This method avoids the inherent selectivity challenges in direct pyrimidine trifluoromethylation. The reaction demonstrates tolerance to various functional groups, yielding 5‐trifluoromethyl pyrimidine derivatives with up to 80% yields. Moreover, the practicality
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Regioselective Synthesis of Multisubstituted Fluoropyrazoles via Silver‐Catalyzed One‐Pot Cyclization Reaction of Diazo Reagents with Fluoronitroalkenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-08 Rong Wang, Jing Nie, Xiaojuan Deng, Guosheng Ding, Fa-Guang Zhang, Jun-An Ma
A silver‐catalyzed regioselective one‐pot cyclization reaction of diazo reagents with fluoronitroalkenes was developed. This transformation presents a method for accessing a series of 4‐aryl‐3‐fluoropyrazoles that are substituted with various groups such as trifluoromethyl, carboxylic ester, nitrile, and phosphonate ester. Further synthetic transformations offered the corresponding fluorinated and
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One‐Pot Synthesis of 2‐Aminothiophenes by Au(I)‐Catalyzed Cascade Reaction Including Hydrothiolation, Thio‐Claisen Rearrangement, and Cycloisomerization Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-07 Yoshihiro Oonishi, Yukiko Ueda, Yoshihiro Sato
The cascade reaction of ynamides with propargyl thiols by Au(I) catalysis involving regioselective hydrothiolation, thio‐Claisen rearrangement, and cycloisomerization to generate 2‐aminothiophenes in a one‐pot manner is described. In this reaction, the selection of reaction temperature is crucial, with the initial step, namely hydrothiolation, conducted at a low temperature (40°C), followed by the
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Enantioselective Friedel‐Crafts Reaction of ortho‐Alkynylnaphthols with Naphthofurans: Synthesis of Polysubstituted Axially Chiral Styrenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-07 Wenxuan Zhang, Jiaying Sun, Daoshan Yang, Ran Song, Wen Si, Jian Lv
Herein, we report a chiral Brønsted acid‐catalyzed enantioselective Friedel‐Crafts reaction of ortho‐alkynylnaphthols with various naphthofurans, realizing the asymmetric synthesis of axially chiral styrenes with naphthofurans in 67 to 93% yield and with 34 to 96% ee.
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Synthesis of Phthalazino[2,3‐a]cinnoline‐6,8,13(5H)‐triones via Ir(III)‐catalyzed Dehydrogenative C‐H/N‐H Functionalization of N‐aryl Phthalazinones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-07 Lin Dong, Chao Zhang, Ling-Xi Zhang
An Iridium(III)‐catalyzed C‐H cyclization of N‐arylphthalazinones with α‐diazotized Meldrum’s acid afforded tetracyclic phthalazine derivatives with a carbonyl group in 98% yield in only 30 min. The initial formation of tetracyclic phthalazine derivatives also provided access to a powerful building block. The utility of this method is emphasized by the synthetic transformation into a series of potentially
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Pd‐Catalyzed [3+6+3+6] Macrocyclizations of Aryl α‐Diazo‐β‐Ketoesters Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-07 Zhuang Zhong, Adiran de Aguirre, Céline Besnard, Amalia I. Poblador-Bahamonde, Jérôme Lacour
Thanks to Pd(II)‐catalysis, an efficient synthesis of unsaturated macrocycles is achieved by [3+6+3+6] condensation of cyclic ethers with aryl α‐diazo‐β‐ketoesters. The presence of the electron‐rich aryl ester moieties forbids the use of dirhodium complexes as these diazo decomposition catalysts provoke unforeseen intermolecular Csp2‐H insertion reactions that derail the targeted reactivity. However
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Accessing SuFExable Cyclobutane‐Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-06 Rongbiao Wei, Guanhua Pei, Yao Huang, Saihu Liao
Indoline‐fused polycycles are commonly found as a key structural component in numerous natural products and biologically active compounds. In recent times, the incorporation of sulfonyl fluoride groups has drawn significant attention in research due to their potential to enhance or confer new biological activities to molecules. In this study, we report the development of a novel and modular approach
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Visible light induced halogen bond assisted Friedel‐Crafts reaction of indole and chalcones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-04 Sunil Kumar, Anupam Das, K. R. Justin Thomas
. The use of halogen bonding interactions as an alternative to acid and metal catalysts for substrate activation has gained popularity in recent years. In this work we demonstrate a halogen bond assisted activation of chalcones under visible light irradiation for the Friedel‐Crafts reaction with indole to yield β‐indolylketones. The simple and scalable protocol uses the readily available CBr4 as halogen
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Brønsted Acid‐Catalyzed Markovnikov Hydroarylation of Arylcyclobutene: A Route to gem‐Diaryl‐Substituted Cyclobutanes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-04 Xiuhong Wang, Zhening Sun, Juanjuan Wang, Zhaojing Zheng, Hong Lu, Hao Wei
A regioselective Markovnikov hydroarylation of arylcyclobutene has been developed using Brønsted acid catalysis through a protonation/Friedel‐Crafts sequence. The metal‐free catalytic reaction is operationally simple and feasible compared to previous reports that utilized elaborate arylcyclobutene and specific polyfluorinated reagents, affording a variety of gem‐diaryl‐ substituted arylcyclobutene
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Decarbonylative and Dehydrogenative Cascade Annulation of N‐(o‐cyanobiaryl)acrylamides with Aldehydes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-03 Cui Zhang, Bo Jiang, Yun-Tao Shen, Wei Jiang, Yu-Song Ran, Tai-Gang Fan, Ya-Min Li
Decarbonylative and dehydrogenative cascade annulation of aldehydes with N‐(o‐cyanobiaryl)acrylamides have been developed for the synthesis of a broad spectrum of alkyl‐ and carbonyl‐substituted pyrido[4,3,2‐gh]phenanthridines. Secondary and tertiary aldehydes can undergo decarbonylative cascade under DTBP/malonic acid conditions, while aryl, primary and secondary aldehydes can undergo dehydrogenative
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Lewis Acid‐Promoted Domino Processes for the Synthesis of Homoallylic Amines, Quinolines and Tetrahydroquinolines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-01 Rahul Vishwakarma, Nagaraju Vodnala, Dulal Musib, Sanjay Singh, Chinmoy Hazra
Herein, the synthesis of homoallylic amines, quinolines, and tetrahydroquinolines has been demonstrated. The domino one‐pot multi‐component approach has been accomplished using Lewis acid‐catalyzed conditions. A useful scaffold construction strategy can be achieved by controlling the electronic effect of aniline rather than relying on reaction conditions. The described method applies to a wide variety
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Enabling Regioselective Synthesis of α‐Methyl BODIPYs via H2O2/DMSO‐Promoted Direct Methylation Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-01 Lv Fan, Shuangshuang Zhu, Zhong-Yuan Li, Wangfei Wang, Hua Wang, Lijuan Jiao, Erhong Hao
Achieving α‐methylation of BODIPYs remains challenging due to the electron‐deficient property of α‐position of BODIPYs. Herein, a H2O2/DMSO‐promoted radical process was employed, providing an approach for the construction of a series of α‐methyl and α,α‐dimethyl BODIPYs in 57‐68% yields. In addition, representative transformations and half‐gram experiments as well as their photophysical properties
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Synthesis of Oxadihydrophenanthroquinolizidinones by Photoinduced Rearrangement of 3‐Biphenyl‐1‐hydroxypropyl‐pyridin‐2(1H)‐ones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-05-01 Jingzhi Sui, Ding Wang, Tao Wang, Kexin Ren, Zunting Zhang
The synthesis of hexahydro‐11H,15H‐dibenzo[f,h] [1,3]oxazino[3,2‐b]isoquinolin‐15‐ones was achieved via photoinduced rearrangement of 3‐biphenyl‐1‐hydroxypropyl‐pyridin‐2(1H)‐ones with a 313 nm UV light. Trans‐(8b,15a)‐9a‐β‐hexahydro‐11H,15H‐dibenzo[f,h][1,3]oxazino[3,2‐b]isoquinolin‐15‐ones and trans‐(8b,15a)‐9a‐α‐hexahydro‐11H,15H‐dibenzo[f,h][1,3] oxazino[3,2‐b]isoquinolin‐15‐ones were obtained
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Acid‐Cooperative Transition Metal‐Catalysed Oxygen‐Atom‐Transfer: Ruthenium‐Catalysed C−H Oxygenation. Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-30 D. Doiuchi, N. Shimoda, K. Okazaki, T. Uchida
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Photochemical Synthesis of Chiral Heterocycles via Asymmetric Carbon‐Heteroatom Bond Formation Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-29 Yogesh Brijwashi Sharma, Sanjukta Saha, Murali Guru
Chiral heterocyclic compounds play a crucial role in the pharmaceutical science, materials science, and agrochemical industries. The critical step for synthesizing chiral heterocycles is the formation of asymmetric carbon‐heteroatom bonds, which can be achieved in a chiral environment under thermal or photochemical conditions. However, photochemical asymmetric transformation has become an area of immense
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Selective Hydro and Deuterodechlorination of Trichloroacetamide under Controlled Electrochemical Conditions to Prepare Mono‐, Di‐, and Deuterochloroacetamides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-27 MANAS BANDYOPADHYAY, Biman Bera, Swastik Pathak, Dipendu Bhunia, Sayan Bhadra, Snehangshu Patra, Manish Pal Chowdhury, Jorge Escorihuela, Mrinal K. Bera
Mono and dichloro acetamides were prepared via hydrodechlorination reaction of trichloroacetamides under controlled electrochemical conditions. The reactions were carried out in an undivided cell with constant current flow using n‐Bu4NI as supporting electrolyte and methanol as solvent and proton source. Deuterodechlorination of trichloroacetamide was also successful using methanol‐d4 as solvent under
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Engineering Styrene Oxide Isomerase Towards Enhanced Chemoenzymatic Synthesis of (S)‐Flurbiprofen Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-26 Willy W. L. See, Joel Ping Syong Choo, Lei Du, Zhi Li
The conventional synthesis of (S)‐flurbiprofen, a valuable non‐steroidal anti‐inflammatory drug (NSAID), involves inefficient chiral resolution with low‐yielding multiple reaction steps, or asymmetric synthesis with low enantioselectivity and/or regioselectivity. Here, we developed high‐yielding, enantioselective, and sustainable synthesis of (S)‐flurbiprofen via two chemoenzymatic approaches from
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Desymmetrization of Cyclohexadienones via [3+2]/[2+1] Domino Annulation: Access to Cyclopropane Fused Tricyclic Enones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-26 Yannan Zhu, Sen Wang, Bo Fang, Qiuyun Li, Gang Qi, Zhongfei Han
A [3+2]/[2+1] domino annulation reaction of cyclohexadienones and α‐aryl vinylsulfonium salts has been reported. A range of cyclopropane fused tricyclic enones bearing four contiguous stereocenters were obtained as a single diastereomer in 44‐93% yields. The synthetic utility was demonstrated with the gram‐scale reactions and further transformations of the products.
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Front Cover Picture: Ru(II) Catalyzed Oxidative Dehydrogenative Annulation and Spirocyclization of Isoquinolones with N‐Substituted Maleimides (Adv. Synth. Catal. 8/2024) Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-26 Kaushik Seal, Biswadip Banerji
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Selectivity Switch in Non‐Directed Palladium‐Catalyzed C‐H Olefination of Chlorobenzene Derivatives Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-25 Jeanne Fichez, Maria Ivana Lapuh, Lina Truong, Hassan Oulyadi, Floris Buttard, Tatiana Besset
A palladium(II)‐catalyzed oxidative C‐H olefination of chlorobenzene derivatives, which favored the functionalization at the ortho‐to‐chlorine position, was reported. The catalytic system employed a commercially available quinoline ligand to access a wide panel of olefinated aryl chlorides in moderate to high yields from feedstock chemicals (42 examples, 28 to 93% yields). The synthetic utility of
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Ambiphilic Reactivity of SF5‐Alkynes Applied to Regioselective and Stereodivergent Halogenation Reactions: An Experimental and Theoretical Case Study Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-25 David Matchavariani, Lucas Popek, Jorge Juan Cabrera Trujillo, Thi Mo Nguyen, Nicolas Blanchard, Karinne Miqueu, Dominique Cahard, Vincent Bizet
We explored the ambiphilic reactivity of SF5‐alkynes, and we proved they can act as both nucleophiles and electrophiles. We selected halogenation reactions as benchmark reactions and developed highly selective stereodivergent hydrohalogenation (I, Br, Cl, F) reactions of SF5‐alkynes. The stereochemistry is finely controlled thanks to the nature of the acids used (strong or soft) in the presence of
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Iron‐Catalyzed C–C and C–N Bond‐Forming Tandem Amidation Offering Access to 3‐Amino‐3‐Aminomethyl‐2‐Oxindole Frameworks Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-25 Shidheshwar Ankade, Chandini Pradhan, Pragnya Samal, Rajesh Gonnade, Sailaja Krishnamurty, Benudhar Punji
An iron‐catalyzed protocol for the synthesis of 3‐amino‐3‐aminomethyl‐2‐oxindole heterocyclic structures is disclosed employing isatins and non‐nucleophilic N‐methoxybenzamides. This reaction class is associated with broad scope and tolerates numerous functionalities, such as fluoro, chloro, bromo, iodo, trifluoromethyl, nitrile, ester, ether, and alkenyl, including heteroaryl ‐ thiophene, benzothiophene
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Three‐Component Palladium‐Catalyzed Tandem Suzuki‐Miyaura/Allylic Substitution: A Regioselective Synthesis of (2‐Arylallyl) Aryl Sulfones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-24 Marina Bellido, Martí Garçon, Xavier Verdaguer, Antoni Riera
A one‐pot Pd‐catalyzed tandem process to prepare (2‐arylallyl) aryl sulfones has been developed. This strategy is based on the modular assembly of a boronic acid, a sodium sulfinate and 2‐bromoallyl acetate. The reaction is completely regioselective towards the terminal alkene, yielding (2‐arylallyl) aryl (or alkyl) sulfones with yields ranging from 56 to 93%. Control experiments together with DFT
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Synthesis of N,N‐Disubstituted Hydrazines by Electrocatalytic Addition of Hydrazines to α,β‐Unsaturated Carbonyl Compounds Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-24 Qingyu Xu, Chengwei Zhang, Hang Xu, Changying Zheng, Yue Li, Sen Xu, Xiaoquan Yao
A strategy for the synthesis of N,N‐disubstituted hydrazines via the electrocatalytic addition of hydrazine to α,β‐unsaturated carbonyl compounds is reported. The reaction was carried out under constant current electrolytic conditions in an undivided cell. Using this methodology, various N,N‐disubstituted hydrazines are prepared with 57‐94% yields in 40 min. By adding cyclohexanone and acetic acid
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Phospholanes via twofold C‐H‐addition to phospholes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-24 Katharina Getfert, Fabian Roesler, Clemens Bruhn, Rudolf Pietschnig
. A synthetic route towards phospholanes via twofold C‐H‐addition of a DMSO molecule to β‐H substituted phospholes is described. The resulting fused phospholane oxothiolane system in case of symmetric α‐substitution possesses four stereogenic centers or rather six in case of asymmetric α‐substitution. The reaction conditions are shown to be applicable for a variety of phospholes with different P‐ or
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Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-24 Sha Peng, Li-Hua Yang, Xiang-Qin Xu, Long-Yong Xie
Herein, we present a (NH4)2S2O8 mediated difunctionalization reaction of aryl alkenes with quinoxalinones and P(O)SH compounds. This method enables the synthesis of various phosphorothioate‐containing quinoxalin‐2(1H)‐one derivatives (46 examples) in 37‐79% yields. The reaction is compatible with a range of functional groups and is easily adaptable to large‐scale synthesis. Preliminary studies suggest
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Selective Hydrosilylation and Hydroboration of Allenes Catalyzed by Cobalt‐Pincer Complexes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-24 Dariusz Lewandowski, Grzegorz Hreczycho
. Achieving precise control over regioselectivity and stereoselectivity in the hydroelementation of terminal allenes presents a formidable challenge. Despite the existence of various catalytic methods for their functionalization, this entire class of reactions remains significantly underdeveloped and demands extensive research. Here, we report a method for the hydroelementation of allenes using inexpensive
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Access to γ‐Iodo‐gem‐Diborylated Cyclopentanes and to Bicyclic Cyclopropanes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-23 Dace Cirule, Fabrice Dénès, Philippe Renaud
A formal atom transfer radical [3+2] annulation (ATRAn) reaction between different homoallyl radical precursors and 1,1‐diborylethene was developed. It provides a rapid access to polysubstituted cyclopentanes containing a gem‐diboronic ester moiety. The synthetic utility of theses uniquely functionalized 5‐membered rings is highlighted by their easy conversion to attractive borylated building blocks
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Recent Advances in the Use of α‐Azidochalcones in Heterocycle Synthesis Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-23 Uma Devi Newar, Dhruba Jyoti Boruah, Ram Maurya
α‐Azidochalcones have emerged as remarkably versatile precursors within organic azides, showcasing a broad spectrum of reactivity as a cornerstone for synthesizing diverse molecular scaffolds. The ongoing progress in this field has opened new opportunities for constructing complex organic molecules through diverse chemical transformations due to the versatile reactivity of α‐azidochalcones for further
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Synthesis of bridged bicyclic systems peri‐annulated to the indole ring: tropane‐fused indoles Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-23 Sergey Antropov, Sofiya Tokmacheva, Irina Levina, Olga Ivanova, Igor Trushkov
Ytterbium(III) triflate catalysed domino reaction of (3‐formyl‐4‐indolyl)‐derived donor‐acceptor cyclopropane with primary amines provides a simple approach to an unprecedented tetracyclic skeleton in which tropane system is peri‐annulated with an indole core. This process involves the formation of an imine and its (3+2)‐cross‐cycloaddition with donor‐acceptor cyclopropane moiety, yielding indole core
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Tetrafluoroethylation of Electron‐Rich Alkenyl Iodides Enabled by in situ Generation of Solvent‐Stabilized “Ligandless” CuCF2CF2H Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-23 Cristina Maria Segovia, Luana L. T. N. Porto, Paula Casasús, Isabel Bascuas, Amena Ahmad, Jordi Mestre, Miguel Bernús Pérez, Sergio Castillon, R. Tom Baker, Omar Boutureira
In this study, we have developed a metal‐mediated synthetic method for incorporating the 1,1,2,2‐tetrafluoroethyl (CF2CF2H) motif into unactivated, electron‐rich alkenyl iodides using cross‐coupling reactions. We discovered that the stable Cu(CF2CF2H)(PPh2Me)3 complex, while unreactive with these substrates, serves as a valuable P‐ligated reservoir for the formation of solvent‐stabilized "ligandless"
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Asymmetric Boracarboxylation of Styrenes Using Carbon Dioxide Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-23 Martin Pettersen, Cuong Dat Do, Sai Manoj N. V. T. Gorantla, Marc F. Obst, Roman Damm, Anggi E. Putra, Ashot Gevorgyan, Ljiljana Pavlovic, Kathrin H. Hopmann, Annette Bayer
The boracarboxylation reaction has potential for production of natural products and drug candidates, but the development of an asymmetric version of this transformation is challenging. We report an enantioselective boracarboxylation of styrenes, enabled by a copper catalyst containing chiral phosphines. Our experimental conditions provide yields between 31‐76% and enantiomeric ratios from 80:20 up
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One‐pot Access to Sulfonyl 2,3‐Diarylnaphthalenes via tBuOK‐Mediated Benzannulation of o‐Bis‐sulfonylmethyl Arenes with Diarylacetylenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-23 Meng-Yang Chang, Nai-Chen Hsueh
One‐pot access to sulfonyl 2,3‐diarylnaphthalenes was developed via tBuOK‐mediated (4+2) benzannulation of o‐bis‐sulfonylmethyl arenes, employing diverse diarylacetylenes. A plausible mechanism is proposed and discussed. The advantages of the system include the use of inexpensive reagents, wide substrate scope, and mild reaction conditions. The synthetic route allows for the formation of two carbon–carbon
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Regioselective C6‐Arylation of Thieno[3,2‐c]pyrazole Heterocycles with Aryl Iodides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-23 Mohamed Abarbri, Noura Ait Lfakir, Badr JISMY, Gérald GUillaumet, Mohamed AKSSIRA, Ahmed El Hakmaoui, Régis Guillot, Abdellatif TIKAD
Efficient and regioselective C6‐arylation of thieno[3,2‐c]pyrazoles with aryl iodides as coupling partners has been developed. This strategy was performed in the presence of Pd(OAc)2 as catalyst in combination with AgOTf as an oxidant and TFA in dimethylacetamide. In all experiments, only the C6‐arylated thieno[3,2‐c]pyrazole was isolated since its C5‐regioisomer was not observed, indicating the high
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I2‐Promoted Oxidative Annulation of Deoxybenzoin‐Chalcone Adduct: Temperature‐Controlled Access to Tetrasubstituted 2,3‐trans‐Dihydrofurans and Furans Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-23 Thi Thanh Nhan Vu, Thu Ngoc Trinh, Thu Trang Pham, Minh Tu Ha, Dinh Hung Mac, pascal retailleau, Thanh Binh Nguyen
Tetrasubstituted 2,3‐trans‐dihydrofuran and furan are important heterocyclic scaffolds in natural product, bioorganic and medicinal chemistry as well as in material science. The synthesis of both of these heterocycles starting from common and readily available starting materials are challenging. We found that in situ generated deoxybenzoin‐chalcone Michael adducts underwent oxidative annulation upon
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Organocatalytic Enantioselective Synthesis of Nitrocyclopropanes Bearing a Thioester Group and Three Stereogenic Centers Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-23 Bingfu Wang, Jian Liu, Hui Jin, Lixin Zhang
A two‐stage protocol was developed for accessing nitrocyclopropanes that bear a thioester group and three stereogenic centers. This protocol achieves practical overall yields ranging from 54% to 75%, along with high levels of stereoselectivity (single diastereomer with up to 98% ee). Brominated monothiomalonate (Br‐MTM) is used as an α‐bromo thioacetate equivalent, which reacts efficiently with nitroolefins
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Visible Light-Enabled Decarboxylative Alkylation of Quinoxalin-2(1H)-ones using Alkyl Carboxylic Acids via Energy Transfer Process Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 Anoop Sharma, Nihal Singh, Raman Kumar, Anuj Sharma
Here in, we describe the photochemical decarboxylative alkylation of quinoxalin-2(1H)-ones using commercially accessible carboxylic acids with oxygen as sole oxidant through energy transfer process. The coupling of diverse array of alkyl carboxylic acids (1o to 3o) and bioactive acids with quinoxalin-2(1H)-ones is successfully accomplished to achieve the desired alkylated products.
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Visible-light mediated Ugi-type reaction for the synthesis of 3,3-disubstituted phthalides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 Feiyu Gao, Chenxin Yin, Yi He, Shuang Zhao, Mengxiao Chen, Jia Zheng, Dan Ni, Houhua Yin, Xian Fu, Xiaoyong Zhang, Shenyou Nie
The synthesis of diverse phthalides containing quaternary carbon centers remains poorly exploited, requiring stepwise reactions with toxic reagents under high temperatures. Herein, we describe a visible-light promoted, photo- and metal-catalyst-free protocol for the modular synthesis of 3,3-disubstituted phthalides with water as the sole by-product. This process featured an open-flask operation of
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Improved Palladium Catalysis in Suzuki-Type Coupling of Benzotriazinones for o-Aryl/Alkenyl Benzamides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 Minling Xü, Ke Xü, Gang Zou
A palladium catalyst system based on PdCl2(PPh3)2 or PdCl2(dppf) is reported for Suzuki-type coupling of both N-aryl and alkyl benzotriazinones with aryl/alkenyl boronic acids to afford a series of ortho-aryl/alkenyl benzamides in yields up to 99%, showing improvements on catalytic efficiency, substrate scope and practicality. Scope and limitations of the improved protocol have been demonstrated with
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A Mild Metal-Free Approach for the Direct Synthesis of Carbamoyl Azides from Carboxylic Acid Redox Active Esters Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 Yan-Hua Qiu, Yuping Zhu, Ming-Hua Rao, Chang-Qi Huang, Zi-Ying Huang, Zhengwang Chen, Jinbin Zhu, Daohong Yu
Carbamoyl azide is an important compound which was transformed into urea, amine and applied to nitrene insertion reaction. We developed a novel metal- and oxidant-free method for the direct synthesis of carbamoyl azide from acid redox active esters. A variety of functional groups were tolerated. In addition, the late-stage modification of natural products and drugs paves the way for the design and
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Copper-catalyzed Alkenylation and Alkenyloxylation with-Alkenyl(phenyl)iodonium Salts Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 Zhao-Xin Song, Meng-Wei Yang, Teng-Teng Wu, Yun-He Xu
An efficient and straightforward Cu-catalyzed vinylation method for alkenyl ethers has been developed. This method demonstrates outstanding performance, delivering high yields and remarkable stereoselectivities for both cyclic and chain alkenyl ether substrates. Furthermore, we have successfully applied this method to directly vinylate the C-2 position of protected glucals, offering a valuable tool
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Synthesis of 2-Amino-3-arylindoles and their Fused Analogues via Intramolecular C-Arylation. Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 K. Žáková, P. Králová, M. Soural
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Gold‐Zinc Co‐Catalyzed Alkynoate Hydrocarboxylation with N‐Protected Amino Acids for Preparation of Storable Acylating Reagents and Racemization‐Free Peptide Synthesis Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 Ayaka Sakurada, Miyu Sato, Kosuke Higashida, Masaya Sawamura
Hydrocarboxylation of methyl 2‐octynoate, a chemical commercially available at a low cost, with N‐protected amino acids was developed with a gold‐zinc cooperative catalyst constructed with a 5‐[(2,2'‐bipyridin)‐5‐yl]imidazo[1,5‐a]pyridin‐3‐ylidene to prepare α‐methoxycarbonyl enol esters as acylating reagents. The α‐methoxycarbonyl enol esters were isolable through silica‐gel column chromatography
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Gold-Catalyzed Synthesis of Ortho-Quinone Methide Analogues as Reactive Synthetic Precursors. Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 T. Yamada, A. Fujii, C. Furugen, K. Kobayashi, T. Hyodo, T. Ikawa, H. Sajiki
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Access to Benzyl Oxindoles via Electron Donor–Acceptor Complex Photoactivation Using Thianthrenium Salts and Potassium Carbonate Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-18 Pau Sarró, Albert Gallego Gamo, Roser Pleixats, Adelina Vallribera, Carolina Gimbert Suriñach, Albert Granados Toda
A photochemical synthesis of biologically relevant benzyl oxindoles is presented via electron-donor acceptor (EDA) complex strategy. This exogenous photocatalyst-free method describes the formation of a new electron donor-acceptor complex based on potassium carbonate and thianthrenium salts for C(sp2)–C(sp3) bond formation. This transition-metal free reaction allows a rapid increase in oxindoles molecular
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Palladium-Catalyzed Two-fold Annulation Reaction of 2,6-Dihalogenobiphenyls with o-Chloroaromatic Carboxylic Acids to Access (Aza)dibenzo[fg,op]tetracenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-17 Ji-Fa Zhu, Song Li, Xin-Yuan Long, Yingbo Shi, Bi-Qin Wang, Chun Feng, Hai-Liang Ni, Shi-Kai Xiang
A palladium-catalyzed two-fold annulation reaction of 2,6-dihalogenobiphenyls with o-chloroaromatic carboxylic acids has been developed. This method enables the synthesis of various dibenzo[fg,op]tetracenes and azadibenzo[fg,op]tetracenes. Preliminary investigations indicate that the resulting product, dimethyl 5,6,12,13-tetrakis(hexyloxy)dibenzo[fg,op]tetracene-2,9-dicarboxylate, demonstrates favorable
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Acid-Mediated Condensation of 2-Aminoaryl Cyclopropyl Ketones with Aldehydes for the Synthesis of 2,3-Dihydrofuro[3,2-c]quinolines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-17 Wenbo Cai, Cong Zhang, Xin Wang, Chuanjun Song
A method for the synthesis of 2,3-dihydrofuro[3,2-c]quinolines via TfOH or TMSOTf mediated condensation of 2-aminoaryl cyclopropyl ketones with aldehydes has been developed. The reaction proceeds under transition metal or halogen free conditions, giving access to the target molecules in 27-90% isolated yields. Mechanistic study indicates that the reaction sequence involves imine formation, intramolecular
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Iridium-Catalysed C(sp3)−H Activation and Hydrogen Isotope Exchange via Nitrogen-Based Carbonyl Directing Groups Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-17 Nathan Knight, James Thompson, John Andrew Parkinson, David Lindsay, Tell Tuttle, William Kerr
Abstract. Growing interest in improved structural diversity within the pharmaceutical industry has led to a focus on more sp3-rich drug frameworks. Meanwhile, spiralling pharmaceutical research and development costs continue to require expedited adsorption, distribution, metabolism, excretion, and toxicity studies, which are heavily reliant on the use of molecules incorporating deuterium and tritium
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Stereoselective access to β‐gem‐difluorinated alcohols through enzymatic reduction Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-17 Lucas Bacheley, Julien Boutet, Gérard Guillamot, Pierre Gilles, Juliette Martin, Phannarath Phansavath, Virginie Ratovelomanana-Vidal
We report here a mild and efficient process to access diversely functionalized enantioenriched b‐gemdifluorinated (S)‐alcohols by using biocatalytic reduction in > 99% yield and enantiomeric excesses ranging from 96% to >99%. This novel approach involves enzymatic reduction of α‐gem‐difluorinated heterocyclic and carbocyclic ketone derivatives as well as an acyclic gem‐difluorinated β‐ketosulfone and
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Manganese‐Mediated Electrooxidative Ring‐Opening Azidation of Cyclobutanol Derivatives with TMSN3 Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-17 Wenchao Gao, Jie Yang, Yong Teng, Wendian Li, Wenguang Li, Ting Li
A Mn‐electrocatalytic ring‐opening azidation of tert‐cyclobutanols has been developed. The regioselective method is applicable for the azidation of a diverse array of cyclobutanols to provide γ‐azido ketones in 23‐91% yields under chemical oxidants‐free reaction conditions. Detailed mechanistic studies suggest the process of Mn‐mediated alkoxy radical generation followed by β‐scission to form carbon‐centered
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Copper‐Catalyzed α‐Indolmethylation of 2‐Pyridylacetates with 3‐Indoleacetic Acids via Alkylideneindolenine Intermediates Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-13 Xiaodong Tang, Chen Chen, Yongjun Chen, Jianxin Pang, Weiya Kong
This study reports the copper‐catalyzed α‐indolmethylation of 2‐pyridylacetates with 3‐indoleacetic acids. This reaction offers a approach to generating alkylideneindolenine electrophiles via the oxidative decarboxylation of 3‐indoleacetic acids. The developed reaction system demonstrates good versatility, extending beyond the indolmethylation of 2‐ pyridylacetates to include activated esters and nitroalkanes
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Cobalt-Catalyzed Annulation of Benzimidates or NH-Benzaldimines with Ynamides: Synthesis of 1-Alkoxy- and 1-Alkyl-3-Aminoisoquinolines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-12 Hamdi Sanaa, Liliane Mimoun, Pascal Retailleau, Elsa Anselmi, Cyril Nicolas, Isabelle Gillaizeau
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Organocatalyzed, Three-Component Construction of Cyanopyrazoles Using Diazoacetonitrile Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-12 Anamika Dhami, Anuj Kumar, Kalathingal Nasreen Hisana, Kishor Mohanan
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Enantioselective Si‐H Insertion of Arylvinyldiazoesters Promoted by Rhodium(I)/Diene Complexes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-12 Ziyan Li, Jian-Guo Liu, Wen-Ping Zhang, Ming-Hua Xu
An enantioselective Si‐H insertion between α‐arylvinyldiazoesters and silanes has been developed by employing rhodium(I)/chiral diene complex as the catalyst. This protocol offers a catalytic asymmetric approach to various chiral silanes containing α‐arylvinyl functionality at room temperature with good enantiocontrol (89‐99% ee). Transformation of the resulting enantiomerically enriched α‐arylvinyl‐α‐silyl
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Synthesis of Alkynylsilanes: A Review of the State of the Art Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-11 Krzysztof Kuciński
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Complexes of Borane and 1,3,5-Triazinane-Derived Carbenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-10 Vladimir O. Smirnov, Vitalij V. Levin, Alexander D. Dilman
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Palladium-Catalyzed/Mn(OAc)3-Mediated 1,2-Diazidation and 1,2-Acetoxy/Hydroxylation of N-Allyl Sulfonamides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-10 Marta Papis, Sara Colombo, Leonardo Lo Presti, Giovanni Poli, Gianluigi Broggini, Julie Oble, Camilla Loro
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Solid-Phase Synthesis of Peptidols via Reductive Cleavage Through a Benzotriazole Linker Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-10 Szu-Hsuan Chen, Hui-Ying Chuang, Chitra Rajavel, Yi Kai Lin, Shu-Han Chang, Pei-Chen Tsai, Hui-Ting Chen, Chung-Ming Sun, Anand Selvaraj, Chai-Lin Kao
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TBHP-Mediated Hydroxyperfluoroalkylation of Alkenes with Perfluoroalkyl Iodides to Construct β-Perfluoroalkyl Alcohols Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-10 Jiantao Zhang, Weiming Zhu, Renhua Su, Duoduo Xiao, Peng Zhou, Kai Chen, Min Zhang, Cui Chen, Weibing Liu