Issue 27, 2013
From the journal:

Organic & Biomolecular Chemistry

Platinum catalysed hydrosilylation of propargylic alcohols†

Catherine A. McAdam,a   Mark G. McLaughlin,a   Adam J. S. Johnston,a   Jun Chen,a   Magnus W. Walterb  and  Matthew J. Cook*a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast, Northern Ireland, UK
E-mail: m.cook@qub.ac.uk
Fax: +44 (0) 28 90976524
Tel: +44 (0) 28 90974682

b Eli Lilly and Company Limited, Erl Wood Manor, Windlesham, Surrey GU20 6PH, UK

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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Article information

DOI
https://doi.org/10.1039/C3OB40496J
Article type
Paper
Submitted
11 Mar 2013
Accepted
10 May 2013
First published
10 May 2013
This article is Open Access
Creative Commons BY license

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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