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Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron "Ate" Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger

Gabriel J. Lovinger, Mark D. Aparece and James P. Morken*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: morkenbc.edu

G. J. Lovinger, M. D. Aparece, J. P. Morken, J. Am. Chem. Soc., 2017, 139, 3153-3160.

DOI: 10.1021/jacs.6b12663 (free Supporting Information)


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Abstract

Catalytic enantioselective conjunctive cross-couplings that employ Grignard reagents provide chiral organoboronic esters in an efficient and highly selective fashion. The use of sodium triflate enables "ate" complex formation and overcomes catalytic inhibition by halide ions.

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Proposed Mechanism for the Pd-Catalyzed Conjunctive Cross-Coupling Reaction



Key Words

benzylboronates, arylation


ID: J48-Y2017