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Cross-Electrophile Coupling of Unactivated Alkyl Chlorides
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Abstract
Alkyl chlorides are bench-stable chemical feed-stocks 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 analogs.