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P III ‐Chelation‐Assisted Indole C7‐Arylation, Olefination, Methylation, and Acylation with Carboxylic Acids/Anhydrides by Rhodium Catalysis
Author(s) -
Qiu Xiaodong,
Wang Panpan,
Wang Dingyi,
Wang Minyan,
Yuan Yu,
Shi Zhuangzhi
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201813182
Subject(s) - rhodium , chemistry , acylation , indole test , regioselectivity , catalysis , reactivity (psychology) , ligand (biochemistry) , combinatorial chemistry , chelation , organic chemistry , methylation , chemoselectivity , medicinal chemistry , medicine , biochemistry , receptor , alternative medicine , pathology , gene
Rhodium‐catalyzed C7‐selective decarbonylative arylation, olefination, and methylation of indoles with carboxylic acids or anhydrides by C−H and C−C bond activation have been developed. Furthermore, C7‐acylation products can also be generated selectively at a lower reaction temperature in the developed system. The key to the high reactivity and regioselectivity of this transformation is the appropriate choice of an indole N ‐P t Bu 2 chelation‐assisted group. This method has many advantages, including easy access and removal of the directing group, the use of cheap and widely available coupling agents, no requirement of an external ligand or oxidant, a broad substrate scope, high efficiency, and the formation of a sole regioisomer.