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Catalytic Dehydrogenative Stannylation of C(sp)-H Bonds Involving Cooperative Sn-H Bond Activation of Hydrostannanes

Francis Forster, Victoria M. Rendón López and Martin Oestreich*

*Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany, Email: martin.oestreichtu-berlin.de

F. Forster, V. M. R. López, M. Oestreich, J. Am. Chem. Soc., 2018, 140, 1259-1262.

DOI: 10.1021/jacs.7b13088 (free Supporting Information)



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Abstract

A heterolytic cleavage of the Sn-H bond in hydrostannanes catalyzed by Ohki-Tatsumi complexes enables the generation of a stannylium-ion-like tin electrophile, that reacts with terminal acetylenes in a dehydrogenative stannylation of the alkyne terminus rather than a hydrostannylation of the C-C triple bond. The scope of this direct C(sp)-H bond stannylation with hydrostannanes is broad.

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proposed mechanism



Key Words

stannylation


ID: J48-Y2018