Chemoselective Reduction of
the Carbonyl Functionality
through Hydrosilylation: Integrating Click Catalysis with Hydrosilylation
in One Pot
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Abstract
Herein
we report the chemoselective reduction of the carbonyl functionality
via hydrosilylation using a copper(I) catalyst bearing the abnormal
N-heterocyclic carbene <b>1</b> with low (0.25 mol %) catalyst
loading at ambient temperature in excellent yield within a very short
reaction time. The hydrosilylation reaction of α,β-unsaturated
carbonyl compounds takes place selectively toward 1,2-addition (CO)
to yield the corresponding allyl alcohols in good yields. Moreover,
when two reducible functional groups such as imine and ketone groups
are present in the same molecule, this catalyst selectively reduces
the ketone functionality. Further, <b>1</b> was used in a consecutive
fashion by combining the Huisgen cycloaddition and hydrosilylation
reactions in one pot, yielding a range of functionalized triazole
substituted alcohols in excellent yields