ortho-OH/NH2-promoted reductive deoxygenation of α,β-unsaturated ketones with HBpin

Abstract

A solvent- and catalyst-free protocol for the selective reductive deoxygenation of α,β-unsaturated ketones with pinacolborane (HBpin) has been developed. ortho-OH/NH₂ 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.