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

Jacob R. Ludwig | Zendy; Eric M. Simmons | Zendy; Steven R. Wisniewski | Zendy; Paul J. Chirik | Zendy

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

Author(s) -

Jacob R. Ludwig,

Eric M. Simmons,

Steven R. Wisniewski,

Paul J. Chirik

Publication year - 2020

Publication title -

organic letters

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02934

Subject(s) - cobalt , chemistry , catalysis , coupling (piping) , inorganic chemistry , organic chemistry , materials science , metallurgy

A cobalt-catalyzed method for the C(sp 2 )-C(sp 3 ) 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, L 1 ) 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.

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