We
report a catalytic method for the direct deoxygenation of various
C–O bond-containing functional groups. Using a Ni(II) pre-catalyst
and silane reducing agent, alcohols, epoxides, and ethers are reduced
to the corresponding alkane. Unsaturated species including aldehydes
and ketones are also deoxygenated via initial formation of an intermediate
silylated alcohol. The reaction is chemoselective for C(sp3)–O bonds, leaving amines, anilines, aryl ethers, alkenes,
and nitrogen-containing heterocycles untouched. Applications toward
catalytic deuteration, benzyl ether deprotection, and the valorization
of biomass-derived feedstocks demonstrate some of the practical aspects
of this methodology.
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