Organosilanes have acquired a reputation as important synthetic reagents. We have previously developed a method for regio- and stereoselective preparation of allylic silanes from readily available allylic alcohols1 and the mechanism of this reaction has now been investigated.2 We propose that the tetrafluoroborate counterion of the palladium catalyst plays an important role in both catalyst activation as well as the transmetallation step. Key intermediates and by-products have been identified as well as the catalyst resting state. Additionally, kinetic analysis gives insight into the nature of the turn-over limiting step.   References (1) Selander, N.; Paasch, J. R.; Szab�, K. J. J. Am. Chem. Soc.  2011 , 133, 409.(2) Larsson, J. M.; Szab�, K. J. J. Am. Chem. Soc.  2013 , 135,  443.

Mechanistic insight into palladium-catalyzed silylation of allylic alcohols

246th National Meeting (2013)

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