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Copper-Catalyzed Coupling of Alkyl Vicinal Bis(boronic Esters) to an Array of Electrophiles

Ningxin Xu, Ziyin Kong, Johnny Z. Wang, Gabriel J. Lovinger and James P. Morken*

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

N. Xu, Z. Kong, J. Z. Wang, G. J. Lovinger, J. P. Morken, J. Am. Chem. Soc., 2022, 144, 17815-17823.

DOI: 10.1021/jacs.2c02817


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Abstract

A neighboring boronate group in vicinal bis(boronic esters) provides a dramatic rate acceleration in transmetalation to copper and thereby enables unprecedented site-selective cross-couplings  allyl, alkynyl, and propargyl electrophiles as well as a simple proton. This cross-coupling operates under practical experimental conditions.


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Key Words

alcohols (oxidation, coupling), allylation, allenes, protodeboronations


ID: J48-Y2022