1,2-Selective Hydrosilylation of Conjugated Dienes

Parker, Sarah E.; Börgel, Jonas; Ritter, Tobias

doi:10.1021/ja5008596

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1,2-Selective Hydrosilylation of Conjugated Dienes

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Börgel, Jonas
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ritter, Tobias
Department of Chemistry and Chemical Biology, Harvard University;
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Parker, S. E., Börgel, J., & Ritter, T. (2014). 1,2-Selective Hydrosilylation of Conjugated Dienes. Journal of the American Chemical Society, 136(13), 4857-4860. doi:10.1021/ja5008596.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-8591-5

Abstract

Selective 1,2-hydrosilylation of 1,3-dienes is a challenging problem in transition metal catalysis. Butadiene, specifically, would be a useful substrate because 3-butenylsilane products have promise as superior coupling reagents for hybrid organic/inorganic materials synthesis. We report the first selective 1,2-hydrosilylation of conjugated dienes including butadiene. Hydrosilylation proceeds through a Pt(II/IV) cycle, and selectivity is generated at a hexacoordinate Pt(IV) complex that favors eta(2)-diene coordination and prevents pi-allyl complex formation.