Article
Chemistry, Organic
Tang Zhen, Pi Chao, Wu Yangjie, Cui Xiuling
Summary: An efficient synthesis of 6-arylindazolo[2,3-alpha]quinolines from 2-aryl-2H-indazoles using sulfoxonium ylides and rhodium(III)-catalyzed C-H activation and cyclization reaction is described. The transformation is highly efficient, tolerant to various functional groups, and does not require an external oxidant, resulting in dimethyl sulfoxide (DMSO) and H2O as the only by-products. Furthermore, the scalability of the reaction demonstrates its practicality in industry.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yuncan Chen, Shan Lv, Ruizhi Lai, Yingying Xu, Xin Huang, Jianglian Li, Guanghui Lv, Yong Wu
Summary: This study demonstrates the efficient coupling of sulfoxonium ylides with thioureas under rhodium catalysis to produce 2-aminothiazoles with good functional group tolerance. This approach provides a convenient method for accessing a variety of 2-aminothiazole derivatives with high chemoselectivity.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Cankun Luo, Zhiqian Lin, Yingdi Hao, Pengfei Jia, Ruizhi Lai, Li Guo, Yuan Yao, Yong Wu
Summary: A rhodium-catalyzed Sommelet-Hauser rearrangement using α-thioesters/α-selenoesters and sulfoxonium ylides has been developed for the synthesis of various sulfur/selenium-containing ortho-substituted aromatic compounds in medium to excellent yields. This reaction highlights the advantages of mild conditions and broad substrate scope.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Yuya Kaieda, Kosuke Yamamoto, Masami Kuriyama, Osamu Onomura
Summary: A rhodium-catalyzed reaction has been developed to convert N-sulfonyl-1,2,3-triazoles and carboxylic esters into 2,5-disubstituted oxazole derivatives under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Rui-Hua Liu, Qi-Chao Shan, Ya Gao, Teck-Peng Loh, Xu-Hong Hu
Summary: An efficient Ag-catalyzed [4 + 1] heteroannulation reaction of enamides with alpha-carbonyl sulfoxonium ylides is disclosed, providing a practical access to a diverse range of multi-functionalized oxazoline derivatives with diastereoselectivity. The synthetic utility of tetra-substituted oxazolines is further demonstrated by useful manipulations into valuable building blocks of pharmaceutical relevance.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Xue-Li Lyu, Shi-Sheng Huang, Yuan-Qiong Huang, Hong-Jian Song, Yu-Xiu Liu, Yong-Qiang Li, Shao-Xiang Yang, Qing-Min Wang
Summary: This study presents a new protocol for the rhodium(III)-catalyzed aldehydic C(sp(2))-H acylmethylation reactions, using sulfoxonium ylides as carbene precursors to generate 1,3-diketones from quinoline-8-carboxaldehydes. The reaction mechanism was elucidated by synthesizing a key intermediate - a five-membered-ring acylrhodium species.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiaofeng Liu, Ying Shao, Jiangtao Sun
Summary: A ruthenium-catalyzed highly chemoselective N-alkylation of 2-pyridones has been developed, providing N-alkylated 2-pyridone derivatives in good yields and excellent N-selectivity. The key to this unprecedented reaction is the use of CpRu(PPh3)(2)Cl as the catalyst and sulfoxonium ylides as the alkylation reagents, which can also be applied to 7-azaindoles with slight variations in reaction conditions. Furthermore, sulfonium ylides are also suitable alkylation reagents for good selectivity in N-alkylation of 2-pyridones.
Article
Chemistry, Organic
Radell Echemendia, Kleber T. de Oliveira, Antonio C. B. Burtoloso
Summary: A novel visible-light-promoted coupling of diazoketones with sulfoxonium ylides, employing a violet light-emitting diode, is described under both batch and continuous flow conditions. This transformation permits the direct synthesis of synthetically useful 1,3-dicarbonyl sulfoxonium ylides.
Article
Chemistry, Applied
Jia-Lin Song, Lin Xiao, Shao-Yong Chen, Yi-Chuan Zheng, Yan-Zhi Liu, Shang-Shi Zhang, Bing Shu
Summary: In this study, Rh(III)-catalyzed C-H bifunctionalization and direct vinylene annulation of sulfoxonium ylides and N-carbamoylindoles with vinylene carbonate was successfully achieved, resulting in a series of naphthalenones containing a beta-ketosulfoxonium ylide moiety, isocoumarins, and pyrimidones. This protocol offers mild conditions, wide substrate scope, and compatibility with different functional groups. Additionally, related applications and preliminary mechanistic investigations were also conducted.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yougen Xu, Yadong Gao, Lebin Su, Haiting Wu, Hao Tian, Majian Zeng, Chunqiu Xu, Xinwei Zhu, Kuangbiao Liao
Summary: In this study, a novel approach that combines high-throughput experimentation (HTE) with machine learning (ML) technologies is presented to achieve selective cross-dimerization of sulfoxonium ylides via iridium catalysis. The method provides a convenient and efficient route for the synthesis of a variety of valuable unsymmetrical E-alkenes with high stereoselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Polymer Science
Sherilyn J. Lu, Songsu Kang, Youngsang Cho, Minseok Choi, Christopher W. Bielawski
Summary: The homopolymerization of (dimethylamino)phenylsulfoxonium ethylide, a substituted sulfoxonium ylide, was reported to produce poly[(1-butene)-ran-(2-butene)-ran-(ethylene)] with good yield and high molecular weight using Ni(II) catalyst. Variation in the monomer-to-catalyst feed ratio allowed control over the molecular weights of the polymers produced. The polymerization mechanism involves chain growth with the addition of ethylide units to growing polymer chains and expulsion of (dimethylamino)phenyl sulfoxide as a byproduct.
JOURNAL OF POLYMER SCIENCE
(2021)
Article
Chemistry, Organic
Hui Zhou, Zengbao Yang, Cankun Luo, Jianglian Li, Li Hai, Yong Wu
Summary: A protocol for Rh(III)-catalyzed C-H activation using sulfoxonium ylides as traceless directing group and acryloyl silanes has been described. The method provides an efficient and convenient approach to construct the tricyclic skeleton of furan-fused indanone by simultaneously forming two C-C bonds and one C-O bond in one pot, with a broad substrate scope. Additionally, controlled C-H alkenylation has been achieved.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Siliang Ming, Jian Yang, Shi Wu, Gang Yao, Hongwei Xiong, Yu Du, Jun Gong
Summary: An efficient asymmetric cyclopropanation reaction has been developed, which involves the reaction of sulfoxonium ylides with alpha,beta-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex. The enantioenriched cyclopropane derivatives, containing three contiguous tertiary stereocenters, were obtained with high yields and excellent stereoselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Jia Jia, Shuai Chen, Ting Mao, Jinlan Li, Weipiao Li, An-Jun Wang, Dezhi Yang, Zhengli Liu, Chun-Yang He, Zhang Feng
Summary: The t-BuONa-promoted method enables the site-selective silylation of 2H-indazoles, resulting in the synthesis of silylated 1H-indazoles and 2H-indazoles controlled by substituents. The use of SEM as a protecting group allows for the deprotection of N-SEM 2H-indazoles and their conversion into silylated 1H-indazoles, thus controlling the site-selective silylation. This protocol demonstrates broad substrate scope and excellent functional group tolerance, with preliminary experimental studies suggesting the involvement of silyl radicals.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Jia Jia, Shuai Chen, Ting Mao, Jinlan Li, Weipiao Li, An-Jun Wang, Dezhi Yang, Zhengli Liu, Chun-Yang He, Zhang Feng
Summary: Herein, we describe a t-BuONa-promoted method for the site-selective silylation of 2H-indazoles. Control over the silylation site is achieved through substituents. Using SEM as a protecting group, the N-SEM 2H-indazoles can be easily deprotected and converted to silylated 1H-indazoles. This protocol shows broad substrate scope and excellent functional group tolerance, with preliminary experimental studies suggesting the involvement of silyl radicals in the reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yaqun Dong, Song Sun, Jin-tao Yu, Jiang Cheng
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Yan Xiao, Song Sun, Jin-Tao Yu, Jiang Cheng
Article
Chemistry, Organic
Song Sun, Cong Zhou, Jiang Cheng
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Chang Wang, Peng-Cheng Qian, Fan Chen, Jiang Cheng
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Yang Li, Zhixin Wang, Shengbo Xu, Jiang Cheng
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Chen Liang, Zhibin Chen, Xinyue Hu, Shengxia Yu, Zhenlian Wang, Jiang Cheng
Summary: We developed a phosphine-catalyzed ring-opening reaction of cyclopropenones with dicarbonyl compounds as C-nucleophiles, leading to 1,3,3'-tricarbonyl compounds. This transition-metal free procedure features mild and neutral reaction conditions with good atom economy, providing an easy pathway to access 1,3,3'-tricarbonyl derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Organic
Lu Wang, Ying Shao, Jiang Cheng
Summary: The cyanation reaction plays a key role in organic chemistry due to the wide applications of nitrile compounds. Traditionally, metal cyanides were used as cyanide sources, but recent research shows the potential of using combined cyanide sources for cyanation reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Shengnan Jin, Fan Chen, Pengcheng Qian, Jiang Cheng
Summary: A new method using DTBP as a promoter allows for the difunctionalization of alpha-aryl alpha-alkynyl allylic alcohols with alkyl nitriles, resulting in alpha-alkynyl gamma-cyano functionalized ketones. This process involves C(sp(3))-H bond cleavage of alkyl nitriles and radical 3-exo-dig cyclization, with a preference for 1,2-alkynyl migration over 1,2-aryl migration.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Organic
Chang Wang, Fan Chen, Pengcheng Qian, Jiang Cheng
Summary: The Rh-catalyzed C-H bond activation/annulation provides a new strategy for the synthesis of new frameworks, with important research significance and application prospects.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Chang Wang, Xiaodong Fan, Fan Chen, Peng-Cheng Qian, Jiang Cheng
Summary: A rhodium-catalyzed annulation of vinylene carbonate with amidines was developed in this paper, leading to 4-methylquinazolines with moderate to excellent yields. The procedure proceeded by sequential ortho-acylation and annulation, utilizing vinylene carbonate as the acetylation reagent.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Zhixin Wang, Yang Li, Fan Chen, Peng-Cheng Qian, Jiang Cheng
Summary: A Bronsted acid-promoted intramolecular cyclization reaction was developed in the presence of TsNHNH2 to synthesize polysubstituted indenes with complexity and diversity. Unlike other reactions, a cationic cyclization pathway was involved in this method, where N-tosylhydrazone served as an electrophile and alkylation reagent.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Organic
Cong Zhou, Miao Li, Jintao Yu, Song Sun, Jiang Cheng
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Shanshan Qiao, Peng-Cheng Qian, Fan Chen, Jiang Cheng
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Yaqun Dong, Jin-Tao Yu, Song Sun, Jiang Cheng
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Yiting Li, Song Sun, Jiang Cheng, Jin-Tao Yu
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)