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

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.

SUBMITTER: Ludwig JR

PROVIDER: S-EPMC7867578 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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

Ludwig Jacob R JR Simmons Eric M EM Wisniewski Steven R SR Chirik Paul J PJ

Organic letters 20200930 3

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 ...[more]

PMID: 32996312

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