Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines.
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.
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, China.
Zhen
Z
Zhang
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, China.
Baoliang
B
Huang
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, China.
Guanyu
G
Qiao
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, China.
Liu
L
Zhu
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, China.
Fan
F
Xiao
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, China.
Feng
F
Chen
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, China.
Bin
B
Fu
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, China.
Zhenhua
0000-0002-6579-1670
Z
Zhang
azides; boron; reaction mechanisms; rhodium; synthetic methods