PhI(OAc)2‑Promoted Site-Selective C–H Chlorination of (Hetero)arenes with p‑Toluenesulfonyl Chloride

An efficient and practical system for metal-free catalytic chlorination of (hetero)­arenes by using readily available and inexpensive TsCl and PhI­(OAc)2 is described. This newly developed protocol has been achieved by the nonsymmetric iodane generated by a combination of PhI­(OAc)2 and TsCl. The br...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2024-10, Vol.26 (41), p.8708-8712
Main Authors: Tang, Junyang, Liu, Yaorong, Qiu, Baojie, Zhang, Zhuo, Zhang, Xingxian
Format: Article
Language:English
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient and practical system for metal-free catalytic chlorination of (hetero)­arenes by using readily available and inexpensive TsCl and PhI­(OAc)2 is described. This newly developed protocol has been achieved by the nonsymmetric iodane generated by a combination of PhI­(OAc)2 and TsCl. The broad substrate scope, good functional group tolerance, excellent regioselectivity, and short reaction times make this method attractive for the late-stage chlorination of complex drug-like scaffolds.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03017