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Silver‐Catalyzed Cross‐Coupling of Isocyanides and Active Methylene Compounds by a Radical Process
Author(s) -
Liu Jianquan,
Liu Zhenhua,
Liao Peiqiu,
Zhang Lin,
Tu Tao,
Bi Xihe
Publication year - 2015
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.201504254
Subject(s) - methylene , isomerization , catalysis , chemistry , combinatorial chemistry , surface modification , ligand (biochemistry) , coupling reaction , photochemistry , organic chemistry , biochemistry , receptor
Isocyanides are versatile building blocks, and have been extensively exploited in CH functionalization reactions. However, transition‐metal‐catalyzed direct CH functionalization reactions with isocyanides suffer from over‐insertion of isocyanides. Reported herein is a radical coupling/isomerization strategy for the cross‐coupling of isocyanides with active methylene compounds through silver‐catalysis. The method solves the over‐insertion issue and affords a variety of otherwise difficult to synthesize β‐aminoenones and tricarbonylmethanes under base‐ and ligand‐free conditions. This report presents a new fundamental CC bond‐forming reaction of two basic chemicals.