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Issue 27, 2013
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Platinum catalysed hydrosilylation of propargylic alcohols

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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.

Graphical abstract: Platinum catalysed hydrosilylation of propargylic alcohols

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Publication details

The article was received on 11 Mar 2013, accepted on 10 May 2013 and first published on 10 May 2013


Article type: Paper
DOI: 10.1039/C3OB40496J
Citation: Org. Biomol. Chem., 2013,11, 4488-4502
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    Platinum catalysed hydrosilylation of propargylic alcohols

    C. A. McAdam, M. G. McLaughlin, A. J. S. Johnston, J. Chen, M. W. Walter and M. J. Cook, Org. Biomol. Chem., 2013, 11, 4488
    DOI: 10.1039/C3OB40496J

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