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Journal Article

Ruthenium-Catalyzed trans-Selective Hydrostannation of Alkynes

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Rummelt,  Stephan M.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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anie_201311080_sm_miscellaneous_information.pdf
(Supplementary material), 5MB

Citation

Rummelt, S. M., & Fürstner, A. (2014). Ruthenium-Catalyzed trans-Selective Hydrostannation of Alkynes. Angewandte Chemie International Edition, 53(14), 3626-3630. doi:10.1002/anie.201311080.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-DA87-7
Abstract
In contrast to all other transition-metal-catalyzed hydrostannation reactions documented in the literature, the addition of Bu3SnH across various types of alkynes proceeds with excellent trans selectivity, provided the reaction is catalyzed by [Cp*Ru]-based complexes. This method is distinguished by a broad substrate scope and a remarkable compatibility with functional groups, including various substituents that would neither survive under the conditions of established Lewis acid mediated trans hydrostannations nor withstand free-radical reactions. In case of unsymmetrical alkynes, a cooperative effect between the proper catalyst and protic functionality in the substrate allows outstanding levels of regioselectivity to be secured as well.