Organic Chemistry Portal



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:

H. Liang, J. P. Morken, J. Am. Chem. Soc., 2023, 145, 9976-9981.

DOI: 10.1021/jacs.3c01677

see article for more reactions


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.

see article for more examples

mechanism for transmetalation

Key Words

Arylation, Negishi Coupling

ID: J48-Y2023