Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling

Jacob R. Ludwig, Eric M. Simmons, Steven R. Wisniewski, Paul J. Chirik

Research output: Contribution to journalArticlepeer-review

Abstract

A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

Original languageEnglish (US)
JournalOrganic letters
Volume23
Issue number3
DOIs
StatePublished - Feb 5 2021

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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