Cross-Electrophile Coupling of Unactivated Alkyl Chlorides

Alkyl chlorides are bench-stable chemical feedstocks that remain among the most underutilized electrophile classes in transition metal catalysis. Overcoming intrinsic limitations of C­(sp3)–Cl bond activation, we report the development of a novel organosilane reagent that can participate in chlorine...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2020-07, Vol.142 (27), p.11691-11697
Main Authors: Sakai, Holt A, Liu, Wei, Le, Chi “Chip”, MacMillan, David W. C
Format: Article
Language:English
Subjects:
Catalysis
Hydrocarbons, Chlorinated - chemistry
Molecular Structure
Nickel - chemistry
Oxidation-Reduction
Photochemical Processes
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Summary:Alkyl chlorides are bench-stable chemical feedstocks that remain among the most underutilized electrophile classes in transition metal catalysis. Overcoming intrinsic limitations of C­(sp3)–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(sp2)–C­(sp3) coupled adducts, including numerous drug analogues.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c04812