Article
Chemistry, Applied
Huaping Xu, Heng Wang, Ze-Feng Xu, Shengguo Duan, Chuan-Ying Li
Summary: A rhodium-catalyzed cascade 1,3-sulfinate migration, intermolecular [3 +2] annulation of 1-sulfonyl-1,2,3-triazoles and indoles was successfully achieved. This reaction provided a one-pot method for the construction of cyclopenta[b]indoles bearing four stereocenters, with yields ranging from 45% to 99% and diastereoselectivities from 1.6:1 to > 20:1. Furthermore, the cyclopenta[b]indoles could be transformed into various functionalized compounds, demonstrating the synthetic value of this migration-annulation strategy in ring system synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Zemin Zhao, Qingyu Tian, Yanhui Chen, Si Wen, Yuqing Zhang, Guolin Cheng
Summary: A base-mediated semihydrogenation of ynamides using p-toluenesulfonyl hydrazide as a hydrogen donor is described, which avoids overhydrogenation and reduction of other functional groups, producing exclusively thermodynamically unfavorable Z-enamides.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xinyu Xu, Mingjie Ou, Yan-En Wang, Tingzhi Lin, Dan Xiong, Fei Xue, Patrick J. Walsh, Jianyou Mao
Summary: In this study, a novel method was developed for the synthesis of 7-azaindoles and 7-azaindolines, which are important in medicinal chemistry. The chemoselectivity of the reaction depends on the counterions used, with different products obtained using LiN(SiMe3)(2) and KN(SiMe3)(2). Various substituents can also be introduced under these conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Luo-Rong Yuan, Shun-Jun Ji, Xiao-Ping Xu
Summary: In this study, a cobalt-catalyzed coupling-cyclization cascade reaction was investigated, which allowed for the synthesis of various spiroindoline compounds by modifying substituents at the N1- and C2-positions in the indole skeleton. Interestingly, the spiroindoline products could undergo despirocyclization in the presence of amines, enabling efficient construction of enamine compounds.
Article
Chemistry, Organic
Pavit Kumar Ranga, Feroz Ahmad, Prashant Nager, Prabhat Singh Rana, Ramasamy Vijaya Anand
Summary: The catalytic application of bis(amino)cyclopropenium ion in conjugate addition reactions has been investigated, with the hydrogen atom on the cyclopropene ring acting as a hydrogen-bond donor catalyst. Experimental studies have verified that the C-H hydrogen in the cyclopropene ring is solely responsible for catalyzing these transformations, activating the carbonyl group of p-quinone methide through hydrogen bonding.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Oleksandr S. Liashuk, Vladyslav A. Andriashvili, Andriy O. Tolmachev, Oleksandr O. Grygorenko
Summary: The chemoselective transformations of functionalized sulfonyl fluorides and chlorides have been comprehensively surveyed. Sulfonyl fluorides show excellent selectivity control in their reactions, while sulfonyl chlorides typically react at the SO2Cl moiety except for a few exceptions.
Review
Chemistry, Multidisciplinary
Wangsheng Liu, Lin Hao, Junmin Zhang, Tingshun Zhu
Summary: Electrosynthesis has gained more attention recently for its potential in replacing chemical oxidants or reductants in molecule-electrode electron transfer. Sulfonyl compounds have been found as practical precursors of several radicals, and electrochemical redox reactions offer green and efficient pathways for activating these compounds.
Article
Chemistry, Organic
Haonan Xiang, Jie Liu, Jieping Wang, Lvqi Jiang, Wenbin Yi
Summary: A method for electrophilic (fluoroalkyl) sulfenylation of nucleophiles through the collaborative use of CTAB and squaric acid to promote deoxygenation of sulfonyl derivatives is reported. Mechanistic studies show that squaric acid significantly reduces the energy barrier in the first step of deoxygenation. This novel method allows for the reduction of a wide range of functionalized sulfonyl chlorides and sulfonic anhydrides and demonstrates a high tolerance to various functional groups.
Article
Chemistry, Applied
Dario Allegue, Javier Santamaria, Alfredo Ballesteros
Summary: In this study, a gold(I)-catalyzed and atom-economical synthesis of ortho-N-indolyl-N-pyrazolylbenzene from 1,2,3-triazapentalenes and ynamides was reported. The reaction involves the cleavage of the triazole ring, formation of an alpha-imino gold carbene intermediate, and an aza-Nazarov-type cyclization with participation of an arene ring. The formal [4+1] heterocycloaddition reaction provides the four-carbon synthon from the ynamide, and indole synthesis can also be achieved in a one-pot procedure from their 1-propargyl-1H-benzotrizaole precursors.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Rajagopal Pothikumar, Chandrasekaran Sivaraj, Kayambu Giridharan, Mahesh Kumar Ravva, Kayambu Namitharan
Summary: In this study, we report a copper/amine catalyzed stereoselective addition of alkynes to ketenimine intermediates generated in situ from the sulfonyl azide-alkyne cycloaddition cascade for the stereoselective synthesis of (Z)-1,3-enynes. Significantly, for the first time, enamine intermediates generated in the copper-catalyzed sulfonyl azide-alkyne cycloaddition reactions have been successfully trapped and isolated as the products. Density functional theory computations have also been performed and found to be consistent with the observed experimental stereoselectivity.
Article
Chemistry, Organic
Yaling Huang, Zisong Qi, Xingwei Li
Summary: This study presents a rhodium-catalyzed highly enantioselective reaction, which enables the access to functionalized indoles with excellent enantioselectivities through the nucleophilic cyclization of 2-alkynylanilines.
Article
Chemistry, Organic
Caijin Zeng, Songjia Fang, Shuqi Guo, Huanfeng Jiang, Shaorong Yang, Wanqing Wu
Summary: A novel and efficient palladium-catalyzed annulation of anilines with bromoalkynes for the synthesis of 2-phenylindoles has been described. This approach features excellent regio- and stereoselectivities and good functional group tolerance. Preliminary mechanistic studies indicate that anilines undergo anti-nucleophilic addition to bromoalkynes to generate (Z)-N-(2-bromo-1-phenyl-vinyl) anilines, followed by sequential C-H functionalization to deliver different substituted 2-phenylindoles. This method provides potential applications for the construction of various biologically active compounds.
Article
Chemistry, Organic
Dong-yu Zhu, Xue-jing Zhang, Ming Yan
Summary: Enantioselective conjugate addition of azlactones to ethylene sulfonyl fluoride has been achieved effectively via cooperative catalysis, providing structurally diverse azlactone sulfonyl fluoride derivatives for drug discovery purposes.
Article
Chemistry, Organic
Mengyao Yu, Linwei Zeng, Gang Xu, Sunliang Cui
Summary: A multicomponent reaction can transform N-indole carboxylic acids, aldehydes, amines, and C2 building blocks into structurally diverse β-indole carboxamide amino amides. The reaction utilizes ynamides and triazenyl alkynes as the C2 building block, and it offers readily available starting materials, high atom economy, and mild reaction conditions. Additionally, the acyl triazene group in the product can be easily transformed into differential groups to enhance structural diversity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ferdinand Taenzler, Jiasu Xu, Sudhakar Athe, Viresh H. Rawal
Summary: This article presents the dearomative (4 + 3) cycloaddition reactions of 3-alkenylindoles with in situ-generated oxyallyl cations, as well as the transformation of the resulting cycloadducts and preliminary investigations into their enantioselective catalysis using imidodiphosphorimidate catalysts.
Article
Chemistry, Physical
Waqar Ahmed, Sheng Zhang, Xiujuan Feng, Xiaoqiang Yu, Yoshinori Yamamoto, Ming Bao
Article
Chemistry, Physical
Yuhui Zhao, Xiujuan Feng, Sheng Zhang, Yoshinori Yamamoto, Ming Bao
Article
Chemistry, Organic
Lifan Zhu, Hongyu Guo, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Zhiheng Zhang, Yi Wang, Wanhui Wang, Yoshinori Yamamoto, Ming Bao, Xiaoqiang Yu
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Multidisciplinary
Yuhui Zhao, Xiujuan Feng, Yanhui Li, Wei Zhang, Yoshinori Yamamoto, Ming Bao
Review
Chemistry, Applied
Sheng Zhang, Yoshinori Yamamoto, Ming Bao
Summary: Utilizing palladium intermediates for aromatic functionalization reactions is a challenging and significant research topic, as it enables selective functionalization reactions on aromatic rings while inhibiting the formation of traditional products.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Wenkuan Li, Sheng Zhang, Xiujuan Feng, Xiaoqiang Yu, Yoshinori Yamamoto, Ming Bao
Summary: This study introduces a strategy for amide C-N bond activation using a ruthenium catalyst, where in situ formed bis-cycloruthenated complexes are demonstrated as key active species with superior oxidative addition ability. The direct C-H bond activation of 2-arylpyridines followed by amide C-N bond activation in the presence of a ruthenium precatalyst resulted in moderate to good yields of monoacylation products, with synthetically useful functional groups remaining intact during the tandem C-H/C-N bond activation reactions.
Article
Chemistry, Multidisciplinary
Jing-Jing Tang, Xiaoqiang Yu, Yi Wang, Yoshinori Yamamoto, Ming Bao
Summary: A visible-light-driven iron-catalyzed nitrene transfer reaction for intermolecular C-N bond formation is developed, showing high yields and a broad substrate scope under mild conditions. Mechanistic studies suggest a radical pathway, with computational studies revealing the importance of visible-light-induced conversion for the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Jixiao Wang, ChuanCheng Zhou, Zhanming Gao, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao
Summary: A PdNPore catalyst has been developed for efficient CO2 conversion into formic acid with a yield of 86%, and it can be easily recovered and reused without loss of catalytic activity. This catalyst also shows hydrogenation capability towards sodium bicarbonate.
Article
Chemistry, Organic
Wenkuan Li, Sheng Zhang, Xiaoqiang Yu, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao
Summary: The study demonstrates a new strategy for the synthesis of chiral indolizidines through Ir-catalyzed asymmetric hydrogenation of cyclic pyridinium salts. The desired chiral products were obtained with high to excellent yields, moderate enantioselectivity, and excellent diastereoselectivity. The enantiomeric purity of the product was improved through recrystallization.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Hongyu Guo, Sheng Zhang, Xiaoqiang Yu, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao
Summary: Palladium and acid cooperative catalysis was proposed as a strategy for the [3 + 2] cycloaddition of acceptor/donor-type diazo compounds with terminal alkynes, resulting in high yields of 2,3,5-trisubstituted furans. This method provides an efficient pathway to prepare furan-containing organosilane and organoboron reagents, while preserving important functional groups during the cycloaddition reaction.
Article
Chemistry, Multidisciplinary
Xitao Zhang, Sheng Zhang, Shihong Li, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao
Summary: This paper describes an unprecedented three-component addition reaction, which allows for the efficient synthesis of gem-dichloroalkane derivatives in mild conditions without affecting important functional groups.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Jing-Jing Tang, Xiaoqiang Yu, Yoshinori Yamamoto, Ming Bao
Summary: A visible-light-promoted and simple iron salt-catalyzed N-arylation was efficiently achieved under external photosensitizer-free conditions. The method features high reactivity, wide substrate scope, and good functional group tolerance.
Article
Chemistry, Multidisciplinary
Ye Lu, Ying Wang, He Li, Peihe Li, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao, Jinghai Liu
Summary: An efficient and highly selective heterogeneous catalyst system using unsupported gold nanopores (AuNPore) was developed for the hydroamination of alkynes. The AuNPore catalyst enabled regioselective hydroamination of alkynes under mild conditions (rt-50 degrees C) without any additives or solvents, yielding Markovnikov imines in satisfactory to excellent yields. The catalyst showed no leaching of gold during the reaction and could be easily recovered and reused without any loss of catalytic activity. A one-pot, two-step procedure using a single AuNPore catalyst was established for the high atom efficiency synthesis of secondary amines from readily available alkynes and anilines.
Article
Chemistry, Multidisciplinary
Ye Lu, Jixiao Wang, Xiujuan Feng, Yanhui Li, Wei Zhang, Yoshinori Yamamoto, Ming Bao
Summary: An efficient and highly selective heterogeneous catalyst system using unsupported palladium nanopores (PdNPore) was developed for nitrile hydrogenation. The PdNPore catalyst demonstrated high activity and excellent selectivity, producing primary amines with satisfactory to excellent yields. The catalyst could be easily recovered and reused without any loss of catalytic activity.
