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Selective Metal-Free Deoxygenation of Unsymmetrical 1,2-Dicarbonyl Compounds by Chlorotrimethylsilane and Sodium Iodide

Ling-Zhi Yuan, Dolor Renko, Ilhem Khelifi, Olivier Provot*, Jean-Daniel Brion, Abdallah Hamze and Mouad Alami*

*BioCIS, Université Paris-Sud, CNRS, équipe labellisée Ligue Contre le Cancer, Université Paris-Saclay, 92290 Châtenay-Malabry, France, Email: olivier.provotu-psud.fr, mouad.alamiu-psud.fr

L.-Z. Yuan, D. Renko, I. Khelifi, O. Provot, J.-D. Brion, A. Hamze, M. Alami, Org. Lett., 2016, 18, 3238-3241.

DOI: 10.1021/acs.orglett.6b01491 (free Supporting Information)


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Abstract

A combination of chlorotrimethylsilane with NaI enables a selective reduction of several unsymmetrically benzil derivatives in good yields at room temperature. Identification of benzoin intermediates is achieved, and a mechanistic radical process is proposed.

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Key Words

deoxygenation


ID: J54-Y2016