1379964-61-0Relevant articles and documents
An analysis of the influences dictating regioselectivity in platinum-catalyzed hydrosilylations of internal alkynes
Rooke, Douglas A.,Menard, Zachary A.,Ferreira, Eric M.
, p. 4232 - 4244 (2014/06/09)
A full account of our studies on internal alkyne hydrosilylations using platinum catalysis is described. We demonstrate that these transformations are highly governed by the electronic characteristics of the alkyne substituents, wherein the hydride will add preferentially to the more electron-deficient alkyne carbon. The steric and coordinative capabilities of the substituents influence the selectivity to a much lesser extent, with propargylic alcohols a lone exception. The choice of silane is relevant in some cases; specific silanes will afford high regioselectivities while others are much less selective. Ultimately, the regioselectivity of addition can be quite predictable using 13C NMR chemical shift data, allowing this reactivity to be incorporated into purposeful reaction design.
Platinum-catalyzed hydrosilylations of internal alkynes: Harnessing substituent effects to achieve high regioselectivity
Rooke, Douglas A.,Ferreira, Eric M.
, p. 3225 - 3230 (2012/05/31)
Rule of thumb: The high yielding title reaction is described with a focus on understanding the factors that govern the regioselectivity of the process (see scheme). Electronic, steric, and functional group properties all influence the selectivity, an understanding of which allows the selective formation of trisubstituted vinylsilanes, which are synthetically useful compounds for accessing stereodefined alkenes. Copyright
