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Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines
Author(s) -
Zhang Zhen,
Huang Baoliang,
Qiao Guanyu,
Zhu Liu,
Xiao Fan,
Chen Feng,
Fu Bin,
Zhang Zhenhua
Publication year - 2017
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.201700539
Subject(s) - tandem , azide , boronic acid , combinatorial chemistry , chemistry , coupling (piping) , organic chemistry , materials science , composite material , metallurgy
Amidine is a notable nitrogen‐containing structural motif found in bioactive natural products and pharmaceuticals. Herein, a novel rhodium(I)‐catalyzed tandem reaction of readily accessible azides with isonitriles and boronic acids via a carbodiimide intermediate is achieved. This protocol offers an alternative approach toward N‐sulfonyl‐, N‐acyl‐, and N‐ phosphoryl‐functionalized, as well as general N‐aryl and N‐alkyl amidines with broad substrate scope. In addition, functionalized guanidines can also been synthesized when amines are used instead. The accomplishment of estrone‐derived amidine and glibenclamide bioisosteres further reveals the practical utility of this strategy.