-OH/NH-promoted reductive deoxygenation of α,β-unsaturated ketones with HBpin.

Org Biomol Chem

School of Chemistry and Material Engineering, Anhui Provincial Key Laboratory of Green Carbon Chemistry, Engineering Research Center of Biomass Conversion and Pollution Prevention of Anhui Educational Institutions, Biomass-derived Functional Oligosaccharides Engineering Technology Research Center of

Published: September 2025


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Article Abstract

A solvent- and catalyst-free protocol for the selective reductive deoxygenation of α,β-unsaturated ketones with pinacolborane (HBpin) has been developed. -OH/NH groups efficiently direct the transformation, affording 2-allylphenols and 2-allylanilines under mild conditions with excellent chemo- and regioselectivity. Mechanistic studies indicate a boron-assisted hydride transfer and carbocation pathway. This work provides a sustainable and practical approach to valuable allylic scaffolds with potential applications in medicinal chemistry and materials science.

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http://dx.doi.org/10.1039/d5ob01345cDOI Listing

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