Site-Selective C-H Functionalization of (Hetero)Arenes Via Transient, Non-Symmetric Iodanes

Overview

Journal Chem

Publisher Elsevier

Date 2019 Apr 30

PMID 31032461

Citations 15

Authors

Stacy C Fosu

Chido M Hambira

Andrew D Chen

James R Fuchs

David A Nagib

Affiliations

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Abstract

A strategy for C-H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc). The utility of this mechanism is demonstrated via -selective chlorination of medicinally relevant arenes, as well as site-selective C-H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.

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