Stereospecific Transformations of Alkylboronic Esters Enabled by Direct Boron-to-Zinc Transmetalation
Hao Liang and James P. Morken*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States,
Email: morken
bc.edu
H. Liang, J. P. Morken, J. Am. Chem. Soc., 2023, 145, 9976-9981.
DOI: 10.1021/jacs.3c01677
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Abstract
Chiral secondary organoboronic esters, when activated with t-butyllithium, undergo efficient stereoretentive transmetalation with either zinc acetate or zinc chloride. The organozinc compounds were found to engage in stereospecific reactions with difluorocarbene, catalytic cross-couplings with palladium-based catalysts, and trifluoromethylation with a copper(III) complex.
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mechanism for transmetalation
Key Words
ID: J48-Y2023
