Abstract
A facile and user-friendly protocol has been developed for the selective synthesis of E-vinyl silanes derived from propargylic alcohols using a PtCl2/XPhos catalyst system. The reaction is generally high yielding and provides a single regioisomer at the β-position with E-alkene geometry. The reaction is extremely tolerant of functionality and has a wide scope of reactivity both in terms of alkynes and silanes used. The catalyst loading has been investigated and it is found that good reactivity is observed at extremely low catalyst loadings. This methodology has also been extended to a one-pot hydrosilylation Denmark-Hiyama coupling.
Highlights
Vinyl silanes are useful intermediates which can undergo a wide range of chemical transformations.[1]
A facile and user-friendly protocol has been developed for the selective synthesis of E-vinyl silanes derived from propargylic alcohols using a PtCl2/XPhos catalyst system
The majority of existing methods do not tolerate the incorporation of further functionality in either the substrate or the silane used, severely limiting their utility in synthesis
Summary
Vinyl silanes are useful intermediates which can undergo a wide range of chemical transformations.[1]. The title compound was prepared according to general procedure A, from 1-(1,3-diphenyl-1H-pyrazol-4yl)prop-2-yn-1-ol 1q (275 mg, 1.01 mmol) and dimethylphenylsilane (150 mg, 1.11 mmol) using PtCl2 (2.7 mg, 0.011 mmol) and XPhos (9.6 mg, 0.020 mmol) in THF (2 mL) which following conversion to the vinyl silane and column chromatography (19 : 1 hexane–EtOAc) afforded 2q (290 mg, 71%) as a colourless oil.
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