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Metal‐Free Meerwein Carboarylation of Alkenes with Anilines: A Straightforward Approach to 3‐Benzyl‐3‐alkyloxindoles
Author(s) -
Tang Shi,
Zhou Dong,
Wang YingChun
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402010
Subject(s) - chemistry , combinatorial chemistry , tandem , metal , benzoyl peroxide , nitrite , organic chemistry , yield (engineering) , materials science , nitrate , metallurgy , composite material , polymerization , polymer
A metal‐free, straightforward carboarylation reaction of alkenes with anilines was developed that proceeds through a radical C–H cyclization. In the presence of benzoyl peroxide (5 mol‐%), tert ‐butyl nitrite, and an array of anilines, a wide variety of N ‐arylacrylamides underwent a tandem Meerwein arylation/C–H cyclization to construct the pharmaceutically important 3‐benzyl‐3‐alkyloxindole scaffold in moderate to good yields.