Benzylic C–H chlorination presents a unique strategy to incorporate a broad array of functional groups at benzylic position via sequential chlorination/substitution reaction. This presentation will describe the recent development of a method for site-selective benzylic chlorination that employs a Cu<sup>I</sup>Cl/bis(oxazoline) catalyst with N-fluorobenzenesulfonimide (NFSI) as the oxidant and KCl as a chloride source. This Cu/NFSI-promoted C–H chlorination reaction exhibits higher benzylic site-selectivity relative to other reported benzylic chlorination methods, and it is compatible with alkylarene substrates bearing diverse substituents. Facile nucleophilic substitution of benzylic chlorides enables net C–H coupling with oxidatively sensitive partners, affording products with new C–O, C–S, and C–N bonds.

Selective chlorination of benzylic C–H bonds and sequential coupling with oxidatively sensitive nucleophiles

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.