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

For the first time, the combination of chlorotrimethylsilane with NaI is used as a selective reducting system toward 1,2-diketones. This combination is successfully evaluated with several unsymmetrically benzil derivatives, which are reduced in good yields and with a total α-regioselectivity at room...

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Bibliographic Details
Published in:Organic letters 2016-07, Vol.18 (13), p.3238-3241
Main Authors: Yuan, Ling-Zhi, Renko, Dolor, Khelifi, Ilhem, Provot, Olivier, Brion, Jean-Daniel, Hamze, Abdallah, Alami, Mouad
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:For the first time, the combination of chlorotrimethylsilane with NaI is used as a selective reducting system toward 1,2-diketones. This combination is successfully evaluated with several unsymmetrically benzil derivatives, which are reduced in good yields and with a total α-regioselectivity at room temperature. Identification of benzoin intermediates is achieved, and a mechanistic radical process is proposed.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01491