Rh(III)-catalyzed [4 + 1] cyclization of aryl substituted pyrazoles with cyclopropanols via C-H activation

Wenxi Chen; Yan Mao; Min Wang; Fei Ling; Changchang Li; Zhangpei Chen; Jinzhong Yao

doi:10.1039/d2ob02001g

Rh(III)-catalyzed [4 + 1] cyclization of aryl substituted pyrazoles with cyclopropanols via C-H activation

Org Biomol Chem. 2023 Jan 25;21(4):775-782. doi: 10.1039/d2ob02001g.

Authors

Wenxi Chen^{1

2}, Yan Mao^{1

2}, Min Wang^{1

2}, Fei Ling¹, Changchang Li², Zhangpei Chen³, Jinzhong Yao²

Affiliations

¹ College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China. lingfei@zjut.edu.cn.
² College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China. jzyao@zju.edu.cn.
³ Center for Molecular Science and Engineering, College of Science, Northeastern University, Shenyang 110819, China. chenzhangpei@mail.neu.edu.cn.

PMID: 36594518
DOI: 10.1039/d2ob02001g

Abstract

A rhodium-catalyzed formal [4 + 1]-cyclization reaction of aryl substituted pyrazoles with cyclopropanols via C-H bond activation/cyclization processes to selectively construct a series of carbonyl functionalized pyrazolo[5,1-a]isoindoles is described. The reaction features good functional group compatibility and a broad substrate scope with respect to both cyclization components with up to 84% yields. Mechanistic studies indicated that the C-H cleavage might be the rate-determining step in this transformation.