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, Multidisciplinary
Wangqin Ji, Hai-Hong Wu, Wenbo Li, Junliang Zhang
Summary: A novel, simple, effective, and rapid synthetic method has been developed for constructing C-2 trifluoromethylated indolinyl ketones via a copper-catalyzed cyclization reaction. The reaction likely involves a radical mechanism through a single-electron transfer process, with broad substrate scope, good functional groups, high diastereoselectivities (up to >20:1), and gram-scale synthesis, making this approach highly attractive.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Dong Gao, Lei Jiao
Summary: This study presents an efficient method for constructing indoline structures with a C2-quaternary stereocenter and controlling the migrating group through aza-semipinacol rearrangement. It enables the divergent access to dearomatized indole derivatives with either a C3- or a C2-quaternary stereocenter.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Junjie Meng, Hui He, Qianru Liu, Hanhong Xu, Huicai Huang, Shao-Fei Ni, Zhaodong Li
Summary: A PdII-catalyzed domino enantioselective desymmetrizative coupling of 7-azabenzonorbornadienes with alkynylanilines is described, which generates valuable functionalized compounds with excellent enantio- and diastereo-selectivity. The method allows the construction of multiple covalent bonds and stereocenters in an efficient and atom-economical manner.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Biochemistry & Molecular Biology
Liangxin Fan, Xinxin Zhu, Xingyuan Liu, Fangyu He, Guoyu Yang, Cuilian Xu, Xifa Yang
Summary: This review summarizes recent developments in the synthesis of these tricyclic indoles with palladium-catalyzed domino reactions and their applications in the total synthesis of representative natural products.
Article
Chemistry, Organic
Enshen Zhang, Chen Chen, Xueling Wang, Jian Wang, Yongjia Shang
Summary: An efficient palladium-catalyzed reaction has been developed for the construction of spirooxindoles containing E-exocyclic double bonds. This reaction exhibits broad functional group tolerance and excellent chemo- and E/Z selectivities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Linhong Zuo, Wusheng Guo
Summary: A Pd-catalyzed decarboxylative approach for the construction of 2-allyl-2,2-diarylacetaldehydes via a dearomative umpolung strategy is presented. The reaction is applicable to various cyclic carbonates or allylic acetates with different functional groups. The reaction can be scaled up to gram-scale without loss of efficiency. Control experiments suggest that the reaction proceeds through a palladium-catalyzed dearomative decarboxylation step followed by an umpolung nucleophilic attack.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Ren-Xiao Liang, Ling-Jie Song, Jin-Bo Lu, Wei-Yan Xu, Chao Ding, Yi-Xia Jia
Summary: The study presents a PdH-catalyzed enantioselective heteroarenyne cycloisomerization reaction and a classical enantioselective 1,5-enyne cycloisomerization of N-vinylpropiolamides, showcasing the synthesis of diverse chiral spiro and fused indoline derivatives as well as chiral 2-pyrrolones with good to excellent enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Jingyu Zhang, Wei Xia, Saskia Huda, Jas S. Ward, Kari Rissanen, Markus Albrecht
Summary: A copper(II)-catalyzed dearomative cyclization amination of N-(2-aminobenzoyl) indoles is described, yielding tetracyclic indolines under mild conditions with good yields. Tetracyclic 5a,6-dihydroindolo[2,1-b]quinazolin-12(5H)-ones are obtained in good to excellent yields (up to 99% yield) by N-Ts bond cleavage using trifluoromethanesulfonic acid (TfOH) mediation. The resulting compounds can be easily functionalized through simple synthetic methods.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Lingbo Han, Xin Wei, Yi Yuan, Lu Bai, Hui Wang, Xinjun Luan
Summary: In this study, a palladium-catalyzed C-H arylation/arene dearomatization reaction was performed in a redox-neutral manner. This domino reaction involved in situ-formed Pd(II) species, phenolic-group-directed C-H activation, biaryl cross-coupling, and naphthol dearomatization, leading to the rapid assembly of spiro[4,5]fluorenes with high yield and good chemoselectivity. Interestingly, the malononitrile-derived spirofluorene 6 showed mechanoresponsive luminescence and its potential application in optical memory devices.
Article
Chemistry, Organic
Kota Sugimoto, Io Mori, Takanari Kato, Koji Yasui, Ban Xu, Choon Hong Tan, Minami Odagi, Kazuo Nagasawa
Summary: In this study, a new method for intramolecular oxidative coupling reaction of oxindoles with beta-dicarbonyls using a guanidinium hypoiodite catalyst was reported. The reaction resulted in the formation of spiro-coupling products in moderate to excellent yields. Furthermore, a chiral hypoiodite catalyst derived from the chiral guanidinium organocatalyst was found to be effective for the challenging asymmetric carbon-carbon bond-forming reaction, leading to the synthesis of optically active spiro[indoline-3,4'piperidines].
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hongbo Qi, Kaiming Han, Shufeng Chen
Summary: This study presents a convenient palladium-catalyzed domino cyclization reaction for the synthesis of bis(benzofuranyl)methane scaffolds bearing all-carbon quaternary center, in which multiple bonds and rings are formed in a single synthetic sequence through a cascade reaction. The approach demonstrates broad substrate scope and good functional-group tolerance, and has been successfully applied to the synthesis of benzofuranyl methyl chromane derivatives.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Applied
Su Chen, Monica Oliva, Luc Van Meervelt, Erik V. Van der Eycken, Upendra K. Sharma
Summary: The study presents a palladium-catalyzed cascade reaction to construct difunctionalized acyl indoles, involving multiple bond formations in a single operational step. Enantioselectivity at a quaternary carbon center is attempted. Additionally, a continuous-flow process is demonstrated for the synthesis of aryl isocyanides within minutes and their telescopic use.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Jia-Hao Xie, Chao Zheng, Shu-Li You
Summary: A novel Pd-catalyzed method for dearomative methoxyallylation of 3-nitroindoles with allyl carbonates has been developed, achieving high yields and diastereoselectivity. The method demonstrates good scalability and practicality with relatively low catalyst loading. Kinetic experiments suggest that the nucleophilic attack of the alkoxide anion is the rate-determining step in this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Zhi-Shi Ye, Jin-Chen Li, Gang Wang
Summary: In this concise review, we summarize the transition metal-catalyzed enantioselective synthesis methods of indoles from 2-alkynyl-anilines.
SYNTHESIS-STUTTGART
(2022)
