Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 4, Pages 1259-1262Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b13088
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Funding
- Deutsche Forschungsgemeinschaft [Oe 249/8-1]
- Consejo Nacional de Ciencia y Tecnologia [295157]
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The catalytic generation of a stannyliumion-like tin electrophile by heterolytic cleavage of the Sn-H bond in hydrostannanes at the Ru-S bond of Ohki-Tatsumi complexes is reported. Reacting these activated hydrostannanes with terminal acetylenes does not lead to hydrostannylation of the C-C triple bond but to dehydrogenative stannylation of the alkyne terminus. The scope of this rare direct C(sp)-H bond stannylation with hydrostannanes is broad, and a mechanism involving a beta-tin-stabilized vinyl cation likely having a bridged structure is presented.
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