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Chemoselective Reduction of the Carbonyl Functionality through Hydrosilylation: Integrating Click Catalysis with Hydrosilylation in One Pot

Sudipta Raha Roy, Samaresh Chandra Sau and Swadhin K. Mandal*

*Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur 741252, India, Email: swadhin.mandaliiserkol.ac.in

S. R. Roy, S. C. Sau, S. K. Mandal, J. Org. Chem., 2014, 79, 9150-9160.

DOI: 10.1021/jo501505j (free Supporting Information)


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Abstract

A chemoselective reduction of the carbonyl functionality via hydrosilylation using low loadings of a copper(I) catalyst bearing an abnormal NHC takes place at ambient temperature in excellent yield within a very short reaction time. The hydrosilylation reaction of α,β-unsaturated carbonyl compounds gives allyl alcohols in good yields. The catalyst can also be used for azide-alkyne cycloadditions.

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Key Words

reduction of carbonyl compounds, phenylsilane


ID: J42-Y2014