B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Hydrosilylation of Vinylcyclopropanes
Peng‐Wei Long, Tao He, Martin Oestreich
Abstract
A hydrosilylation of vinylcyclopropanes (VCPs) catalyzed by the strong boron Lewis acid B(C6F5)3 is reported. For the majority of VCPs, little or no ring opening of the cyclopropyl unit is observed. Conversely, for VCPs with bulky R groups, such as ortho-substituted aryl rings or branched alkyl residues, ring opening is the exclusive reaction pathway. This finding is explained by the thwarted hydride delivery to a sterically shielded, β-silicon-stabilized cyclopropylcarbinyl cation intermediate.
Topics & Concepts
HydrosilylationChemistrySteric effectsRing (chemistry)CatalysisHydrideMedicinal chemistryBoronLewis acids and basesAlkylArylStereochemistryOrganic chemistryHydrogenOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsCoordination Chemistry and Organometallics