Cross-Electrophile Coupling of Unactivated Alkyl Chlorides

Holt A. Sakai, Wei Liu, Chi Le, David W.C. MacMillan

Research output: Contribution to journalArticle

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(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.

Original languageEnglish (US)
Pages (from-to)11691-11697
Number of pages7
JournalJournal of the American Chemical Society
Volume142
Issue number27
DOIs
StatePublished - Jul 8 2020

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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