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Brønsted Acid Catalyzed Oxygenative Bimolecular Friedel–Crafts‐type Coupling of Ynamides
Author(s) -
Patil Dilip V.,
Kim Seung Woo,
Nguyen Quynh H.,
Kim Hanbyul,
Wang Shan,
Hoang Tuan,
Shin Seunghoon
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612471
Subject(s) - nucleophile , chemoselectivity , chemistry , friedel–crafts reaction , brønsted–lowry acid–base theory , carbene , catalysis , silylation , synthon , coupling (piping) , combinatorial chemistry , phenols , metal , medicinal chemistry , organic chemistry , materials science , metallurgy
A non‐metal approach for accessing α‐oxo carbene surrogates for a C−C bond‐forming bimolecular coupling between ynamides and nucleophilic arenes was developed. This acid‐catalyzed coupling features mild temperature, which is critical for the required temporal chemoselectivity among nucleophiles. The scope of nucleophiles includes indoles, pyrroles, anilines, phenols and silyl enolethers. Furthermore, a direct test of S N 2′ mechanism has been provided by employing chiral N,N′‐dioxides which also enlightens the nature of the intermediates in related metal‐catalyzed processes.