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Base-Free Dehydrogenative Coupling of Enolizable Carbonyl Compounds with Silanes

C. David F. Königs, Hendrik F. T. Klare, Yasuhiro Ohki*, Kazuyuki Tatsumi* and Martin Oestreich*

*Technische Universität Berlin, Germany; Nagoya University, Japan, Email: martin.oestreichtu-berlin.de, ohkichem.nagoya-u.ac.jp, i45100anucc.cc.nagoya-u.ac.jp

C. D. F. Königs, H. F. T. Klare, Y. Ohki, K. Tatsumi, M. Oestreich, Org. Lett., 2012, 14, 2842-2845.

DOI: 10.1021/ol301089r (free Supporting Information)


Abstract

A tethered ruthenium complex with a Ru-S bond catalyzes a dehydrogenative coupling between enolizable carbonyl compounds and equimolar amounts of triorganosilanes. The complex plays a dual role by activating the Si-H bond to release a silicon electrophile and by abstracting an α-proton from the intermediate silylcarboxonium ion, only liberating dihydrogen as the sole byproduct.

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Key Words

Silyl enol ethers


ID: J54-Y2012-1770