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Internal Oxidant‐Triggered Aerobic Oxygenation and Cyclization of Indoles under Copper Catalysis
Author(s) -
Huang Huawen,
Cai Jinhui,
Ji Xiaochen,
Xiao Fuhong,
Chen Ya,
Deng GuoJun
Publication year - 2016
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.201508076
Subject(s) - chemistry , catalysis , indole test , oxime , surface modification , copper , combinatorial chemistry , atom economy , oxidative phosphorylation , organic chemistry , biochemistry
Abstract A concise synthesis of pyrazolo[1,5‐a]indole derivatives by copper‐catalyzed aerobic oxygenation and cyclization of indoles with oxime acetates is described. This protocol represents an elegant example of N‐1, C‐2, and C‐3 tri‐functionalization of indoles in one‐pot. Mechanistic studies indicate the reaction proceeds through a radical procedure. Oximes as an internal oxidant have been demonstrated to be a driver to initiate aerobic oxidation, which provides a new oxidative pattern for C‐H functionalization even with high atom‐ and step‐economy.