Premium
Visible‐Light‐Driven Aza‐ ortho ‐quinone Methide Generation for the Synthesis of Indoles in a Multicomponent Reaction
Author(s) -
Liu YiYin,
Yu XiaoYe,
Chen JiaRong,
Qiao MingMing,
Qi Xiaotian,
Shi DeQing,
Xiao WenJing
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201704690
Subject(s) - quinone methide , chemistry , cycloaddition , alkyl , quinone , photochemistry , substrate (aquarium) , radical , halide , combinatorial chemistry , functional group , visible spectrum , organic chemistry , catalysis , materials science , oceanography , polymer , optoelectronics , geology
A visible‐light‐driven radical‐mediated strategy for the in situ generation of aza‐ ortho ‐quinone methides from 2‐vinyl‐substituted anilines and alkyl radical precursors is described. This process enables an efficient multicomponent reaction of 2‐vinylanilines, halides, and sulfur ylides, and has a wide substrate scope and good functional group tolerance. Treatment of the cycloaddition products with a base leads to densely functionalized indoles in a single‐flask operation.