Synthesis 2018; 50(02): 330-340
DOI: 10.1055/s-0036-1588576
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed One-Pot Synthesis of N-Sulfonyl, N-Phosphoryl, and N-Acyl Guanidines

Guanyu Qiao
Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China   Email: zhangzhh@cau.edu.cn
,
Zhen Zhang
Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China   Email: zhangzhh@cau.edu.cn
,
Baoliang Huang
Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China   Email: zhangzhh@cau.edu.cn
,
Liu Zhu
Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China   Email: zhangzhh@cau.edu.cn
,
Fan Xiao
Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China   Email: zhangzhh@cau.edu.cn
,
Zhenhua Zhang*
Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China   Email: zhangzhh@cau.edu.cn
› Author Affiliations
This project is supported by the National Natural Science Foundation of China (No. 21672256), the National S&T Pillar Program of China (2015BAK45B01), and Chinese Universities Scientific Fund (2017QC152).
Further Information

Publication History

Received: 06 July 2017

Accepted after revision: 31 August 2017

Publication Date:
12 October 2017 (online)

Abstract

An efficient palladium-catalyzed cascade reaction of azides with isonitrile and amines is presented; it offers an alternative facile approach toward N-sulfonyl-, N-phosphoryl-, and N-acyl-functionalized guanidines in excellent yield. These series of substituted guanidines exhibit potential biological and pharmacological activities. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated by silica gel column flash chromatography in moderate yield.

Supporting Information

 
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