Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines
Zhen Zhang
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorBaoliang Huang
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorGuanyu Qiao
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorLiu Zhu
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorFan Xiao
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorFeng Chen
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorProf. Dr. Bin Fu
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenhua Zhang
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorZhen Zhang
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorBaoliang Huang
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorGuanyu Qiao
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorLiu Zhu
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorFan Xiao
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorFeng Chen
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorProf. Dr. Bin Fu
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenhua Zhang
Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193 China
Search for more papers by this authorAbstract
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.
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