Work

Cross-Electrophile Coupling of Unactivated Alkyl Chlorides

Year: 2020

Type: article

Abstract: Alkyl chlorides are bench-stable chemical feedstocks that remain among the most underutilized electrophile classes in transition metal catalysis. Overcoming intrinsic limitations of C(sp 3 )–Cl bond activation, we report the development of a novel organosilane reagent that can participate in chlorine atom abstraction under mild photocatalytic conditions. In particular, we describe the application of this mechanism to a dual nickel/photoredox catalytic protocol that enables the first cross-electrophile coupling of unactivated alkyl chlorides and aryl chlorides. Employing these low-toxicity, abundant, and commercially available organochloride building blocks, this methodology allows access to a broad array of highly functionalized C(sp 2 )–C(sp 3 ) coupled adducts, including numerous drug analogues.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.0c04812

Authors: Holt A. Sakai, Wei Liu, Chi “Chip” Le, David W. C. MacMillan

Institution: Princeton University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green