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Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines

Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines

Authors :
Guanyu Qiao
Liu Zhu
Zhen Zhang
Chen Feng
Fan Xiao
Bin Fu
Zhenhua Zhang
Baoliang Huang
Source :
Angewandte Chemie (International ed. in English). 56(15)
Publication Year :
2017

Abstract

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.

Details

ISSN :
15213773
Volume :
56
Issue :
15
Database :
OpenAIRE
Journal :
Angewandte Chemie (International ed. in English)
Accession number :
edsair.doi.dedup.....94e0e75b87e4a01f8b30d81ff8b88d0f