Efficient access to 1,3,4-trisubstituted pyrroles via gold-catalysed cycloisomerization of 1,5-diynes

Qiuling Wan; Luoting Xin; Jian Zhang; Xueliang Huang

doi:10.1039/d1ob02393d

Efficient access to 1,3,4-trisubstituted pyrroles via gold-catalysed cycloisomerization of 1,5-diynes

Org Biomol Chem. 2022 Feb 23;20(8):1647-1651. doi: 10.1039/d1ob02393d.

Authors

Qiuling Wan¹, Luoting Xin², Jian Zhang², Xueliang Huang³

Affiliations

¹ College of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian 350007, P. R. China.
² State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, P. R. China. zhj@fjirsm.ac.cn.
³ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081, China. huangxl@hunnu.edu.cn.

PMID: 35137761
DOI: 10.1039/d1ob02393d

Abstract

A gold-catalysed cycloisomerization of 1,5-diynes is described, which offers a selective approach to access 1,3,4-trisubstituted pyrroles. In this reaction, the cationic gold catalyst activates the ynamide moiety, initiating the cycloisomerization to produce the pyrrole core, and H₂O acts as an external nucleophile to trap the vinyl cationic species, thus leading to the formation of 1,3,4-trisubstituted pyrroles with high selectivity.

Publication types

Research Support, Non-U.S. Gov't