Article
Chemistry, Multidisciplinary
Rong Fan, Shihan Liu, Qiang Yan, Yun Wei, Jingwen Wang, Yu Lan, Jiajing Tan
Summary: Boronic acids are widely used reagents in organic synthesis, and this study demonstrates their potential as efficient substitutes for hydroxides when activated through fluoride complexation. The researchers developed a novel reaction involving aryne-induced ring-opening of cyclic sulfides and three-component coupling of fluoro-azaarenes to showcase this application. The novel hydroxy source exhibits mild activation conditions, useful functionality tolerance, and structural tunability, offering new possibilities for organoboron chemistry. Detailed computational studies shed light on the mechanistic pathway and reactivity differences of ArB(OH)(x)F-y complexes, supporting the experimental data.
Article
Chemistry, Organic
Subrata Bhattacharjee, Shiksha Deswal, Niket Manoj, Garima Jindal, Akkattu T. Biju
Summary: This study demonstrates a facile synthesis of biologically important S-aryl dithiocarbamates through aryne three-component coupling, and presents preliminary mechanistic experiments. Additionally, a unique four-component coupling reaction was observed.
Article
Chemistry, Organic
Xing-Long Zhang, Rui-Li Guo, Meng-Yue Wang, Bao-Yin Zhao, Qiong Jia, Jin-Hui Yang, Yong-Qiang Wang
Summary: The unprecedented palladium-catalyzed three-component dehydrogenative cascade coupling method introduces a C5 structural unit into indoles with high selectivity and a broad substrate scope, making it an economical and efficient approach.
Article
Chemistry, Multidisciplinary
Haiting Ji, Dengkai Lin, Lanzhu Tai, Xinyu Li, Yuxuan Shi, Qiaorong Han, Liang-An Chen
Summary: In this study, a highly enantioselective coupling reaction of acid chlorides with alpha-bromobenzoates was discovered, which can produce enantioenriched protected alpha-hydroxy ketones. The method avoids the use of preformed acyl-metal reagents and has high synthetic utility for the synthesis of other organic compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yangang Wu, Wenbo Cai, Lulu Yu, Junbiao Chang, Chuanjun Song
Summary: A literature-unprecedented three-component aryne coupling reaction has been developed, utilizing pyrroline, imine, dihydroisoquinoline, imidazoline or oxazoline as nucleophiles and acrylonitrile as a third component, which acts as both a proton donor and a nucleophile.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yanling Zheng, Yang Long, Huihua Gong, Jiaqi Xu, Chunchun Zhang, Haiyan Fu, Xueli Zheng, Hua Chen, Ruixiang Li
Summary: In this study, the divergent transformations of 1,3-diols with arylhydrazines were reported, which selectively synthesized pyrazoles and 2-pyrazolines via acceptorless dehydrogenative coupling reactions using Ru3(CO)12/NHC-phosphinephosphine catalytic systems. The reactions showed low catalyst loading, high selectivity, wide substrate scope, and good yields, with only water and hydrogen gas (H2) as the byproducts.
Article
Chemistry, Multidisciplinary
Avishek Guin, Subrata Bhattacharjee, Akkattu T. Biju
Summary: This study demonstrates the direct C2-functionalization of pyridines through a transition-metal-free protocol using aryne multicomponent coupling. The reaction allows for the synthesis of C2-substituted pyridine derivatives bearing the -CF3 group in good yields, with activated keto esters also being employed as third components in the formal 1,2-di(hetero)arylation of ketones. Performing the reaction under dilute conditions inhibits the competing pyridine-aryne polymerization pathway, leading to the desired products.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Junjie Fan, Xiaoyan Wu, Chunling Fu, Shengming Ma
Summary: Here we report a Cp*RhCl2-catalyzed three-component coupling cyclization of 2,3-allenoic acids and 2,3-allenols in the presence of Cu(OAc)(2)center dot H2O, resulting in the formation of furanone derivatives. The synthetic potential of this reaction has been demonstrated, and isotopic labeling experiments have revealed unexpected reaction pathways.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Anil Balajirao Dapkekar, Gedu Satyanarayana
Summary: Here, an efficient electrochemical method is presented for synthesizing 2-alkyl-4-phenylalkan-2-ols through the cathodic reductive coupling of terminal and internal acetylenes with unactivated aliphatic ketones. The process involves the activation of aryl acetylene by a ketyl radical and complete reduction of the triple bond of the acetylene moiety. This environmentally friendly strategy has a broad substrate scope with readily available starting materials.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Fei Wang, Zhiwen Deng, Yawen Wang, Fanshu Yuan, Xing Zhang, Guo-Ping Lu, Ninghua Fu, Yamei Lin
Summary: A KOtBu-mediated strategy has been developed for pyrimidine synthesis via selective three-component coupling reactions. This method allows the synthesis of a variety of pyrimidines with moderate to excellent yields, showing potential for large-scale production due to its metal-free conditions and atom economy.
Article
Chemistry, Multidisciplinary
Satyanarayana Battula, Aman A. Desai, Jigar Y. Soni, Dhruv P. Mehta
Summary: This study presents a novel finding that aldehyde in 2-oxoaldehyde exhibits different behaviors when reacting with Grignard reagents and organocuprate reagents. Additionally, a copper-catalyzed oxidative cross-coupling reaction provides an efficient method for the synthesis of 1,2-diones at room temperature.
Article
Chemistry, Organic
Shiqi Liu, Kun Zhang, Yutong Meng, Jiaxi Xu, Ning Chen
Summary: In this study, a highly efficient and convergent synthetic approach for the construction of tetrahydroisoquinoline-fused polyheterocycles is reported, utilizing a three-component formal [2 + 2 + 2] annulation process. The reaction involves the combination of 3,4-dihydroisoquinolines, CO2, and benzynes, with electron-rich 3,4-dihydroisoquinolines and electron-deficient benzynes showing greater reactivity. This method benefits from the convergent synthesis and the utilization of carbon dioxide, providing a valuable strategy for the facile synthesis of tetrahydroisoquinoline-fused polyheterocycles, with potential applications in the discovery and development of novel organic molecules.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jun Tang, Jingxi He, Sheng-Yin Zhao, Weiping Liu
Summary: Here, we report a manganese-catalyzed three-component coupling reaction for the synthesis of beta,beta-methylated/alkylated secondary alcohols. Our method efficiently constructs assembled alcohols with high chemoselectivity in moderate to good yields using a series of 1-arylethanol, benzyl alcohol derivatives, and methanol. Mechanistic studies suggest that the reaction proceeds via methylation of a benzylated secondary alcohol intermediate to generate the final product.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Valeriia Hutskalova, Christof Sparr
Summary: The study explores the aryne-imine-aryne coupling reaction combined with acridane oxidation for the efficient synthesis of various acridinium salts. The photophysical properties of the novel photocatalysts were investigated and their practical value was demonstrated by a cation-radical accelerated nucleophilic aromatic substitution reaction.
Article
Chemistry, Multidisciplinary
Hemanta Hazarika, Kangkana Chutia, Babulal Das, Pranjal Gogoi
Summary: An aryne-based synthetic protocol has been developed for the synthesis of 3-substituted-3-hydroxy-indolin-2-ones, yielding a wide variety of products in good yields. One of the synthesized compounds has been confirmed by single crystal XRD analysis. Treating the synthesized derivatives with an inorganic base at high temperature leads to an interesting o-arylated product of 1,3-cyclohexandione.
NEW JOURNAL OF CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Santigopal Mondal, Santhivardhana Reddy Yetra, Subrata Mukherjee, Akkattu T. Biju
ACCOUNTS OF CHEMICAL RESEARCH
(2019)
Article
Chemistry, Organic
Arghya Ghosh, Atanu Patra, Subrata Mukherjee, Akkattu T. Biju
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Rahul N. Gaykar, Subrata Bhattacharjee, Akkattu T. Biju
Article
Chemistry, Physical
Tamal Kanti Das, Avik Ghosh, Kuruva Balanna, Pradipta Behera, Rajesh G. Gonnade, Udaya Kiran Marelli, Abhijit Kumar Das, Akkattu T. Biju
Article
Chemistry, Multidisciplinary
Tony Roy, Anu Jacob, Subrata Bhattacharjee, Akkattu T. Biju
CHEMISTRY-AN ASIAN JOURNAL
(2019)
Article
Chemistry, Organic
Avishek Guin, Rahul N. Gaykar, Subrata Bhattacharjee, Akkattu T. Biju
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Subrata Bhattacharjee, Anjali Raju, Rahul N. Gaykar, Rajesh G. Gonnade, Tony Roy, Akkattu T. Biju
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Article
Chemistry, Organic
Rahul N. Gaykar, Malini George, Avishek Guin, Subrata Bhattacharjee, Akkattu T. Biju
Summary: This study presents an oxa-[2,3] sigmatropic rearrangement involving arynes, with the reversal of the C=O bond polarity in ketones. The in situ-generated sulfur ylides from beta-keto thioethers and arynes undergo efficient rearrangement to synthesize functionalized enol ethers with high yields and excellent functional group compatibility. Preliminary mechanistic studies suggest that a Pummerer-type rearrangement is not operating in this case.
Article
Chemistry, Multidisciplinary
Avishek Guin, Subrata Bhattacharjee, Akkattu T. Biju
Summary: This study demonstrates the direct C2-functionalization of pyridines through a transition-metal-free protocol using aryne multicomponent coupling. The reaction allows for the synthesis of C2-substituted pyridine derivatives bearing the -CF3 group in good yields, with activated keto esters also being employed as third components in the formal 1,2-di(hetero)arylation of ketones. Performing the reaction under dilute conditions inhibits the competing pyridine-aryne polymerization pathway, leading to the desired products.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Subrata Bhattacharjee, Shiksha Deswal, Niket Manoj, Garima Jindal, Akkattu T. Biju
Summary: This study demonstrates a facile synthesis of biologically important S-aryl dithiocarbamates through aryne three-component coupling, and presents preliminary mechanistic experiments. Additionally, a unique four-component coupling reaction was observed.
Article
Chemistry, Organic
Rahul N. Gaykar, Shiksha Deswal, Avishek Guin, Subrata Bhattacharjee, Akkattu T. Biju
Summary: This study demonstrates the synthesis of 2,4,5-trisubstituted oxazoles through a transition-metal-free chemical reaction under mild conditions. The desired products were obtained through a series of reaction steps.
Article
Chemistry, Organic
Subrata Bhattacharjee, Avishek Guin, Rahul N. Gaykar, Akkattu T. Biju
Article
Chemistry, Multidisciplinary
Tony Roy, Rahul N. Gaykar, Subrata Bhattacharjee, Akkattu T. Biju
CHEMICAL COMMUNICATIONS
(2019)