PhI(OAc)<sub>2</sub>-Promoted Site-Selective C–H Chlorination of (Hetero)arenes with <i>p</i>-Toluenesulfonyl Chloride
Junyang Tang, Yaorong Liu, Baojie Qiu, Zhuo Zhang, Xingxian Zhang
Abstract
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.
Topics & Concepts
ChemistryCatalysisChlorideMedicinal chemistryMetalOrganic chemistryOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions