Palladium-Catalyzed Gem-Diborylalkylation of Silyl Enol Ethers and N-Vinylacetamide via Diboryl Carbon-Centered Radicals.

Adv Sci (Weinh)

Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N Zhongshan Road, Shanghai, 200062, China.

Published: July 2025


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Article Abstract

Herein, a palladium-catalyzed coupling of gem-iododiborylalkanes with electron-rich olefins to access β,β-diboryl ketones and aldehydes under mild conditions is reported. This method exhibits broad substrate scope and excellent functional group tolerance. Mechanistic studies support a distinctive pathway involving gem-diboryl carbon-centered radicals and a Pd(0)/Pd(I) catalytic cycle, without the formation of Pd(II) intermediates. This protocol provides a new platform for accessing synthetically valuable gem-diboryl carbonyl compounds and expands the reactivity profile of organoboron-based radical transformations.

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http://dx.doi.org/10.1002/advs.202508566DOI Listing

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