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By S.L.& Peppas, N.A.(eds.) Cooper

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Based on kinetic data, the reaction of 54 with alkene and silane is more likely to proceed via the concerted transition state 56 rather than two distinct oxidative addition and insertion elementary steps. Hydrosilylation of styrene with Et3SiH catalysed by 51 (formed in situ from Pt(norbornene)3 and SIMes·HCl/KOtBu) also gave excellent conversions (~99%) with high selectivity (ca. 82%) to the anti-Markovnikov product [45]. The hydrosilylation of alkynes has also been studied using as catalysts Pt, Rh, Ir and Ni complexes.

Cavallo and C. S. J. 14 Tolman electronic parameter (TEP) versus the average CO stretching frequency (nav) for NHCs (■) and phosphines (●). For clarity purposes, only data for the most popular NHCs are labelled Finally, it is also worth mentioning the abnormal NHC ligand of Fig. 15, which extends the nav range to the low value of 2003 cm−1 [71]. 3 Steric Properties of NHCs Based on the experience with tertiary phosphines, the importance of the steric properties of NHC ligands in determining chemical behaviour has been immediately recognised.

In general, catalysts with less bulky NHC ligands are more active. g. 1-hexyne), high conversions under mild conditions were obtained, and in some cases very good selectivities for the b-Z-vinylsilane. In contrast, the hydrosilylations of Et3SiC≡CH gave predominantly the b-E-vinylsilane. These data have been rationalised by postulating the classical Chalk-Harrod hydrosilylation mechanism (Si–H oxidative addition followed by alkyne insertion into the M–Si bond to give intermediate 63 and reductive elimination to the product b-E-vinylsilane).

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