Platinum catalysed hydrosilylation of propargylic alcohols

Catherine A. McAdam; Mark G. McLaughlin; Adam J.S. Johnston; Jun  Chen; Magnus W. Walter; Matthew J. Cook

doi:10.1039/C3OB40496J

Platinum catalysed hydrosilylation of propargylic alcohols

Catherine A. McAdam, Mark G. McLaughlin, Adam J.S. Johnston, Jun Chen, Magnus W. Walter, Matthew J. Cook^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

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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 ß-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.

Original language	English
Pages (from-to)	4488-4502
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	27
Early online date	10 May 2013
DOIs	https://doi.org/10.1039/C3OB40496J
Publication status	Published - 21 Jul 2013

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

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10.1039/C3OB40496JLicence: CC BY

Platinum catalysed hydrosilylation of propargylic alcohols
© The Royal Society of Chemistry 2013 This is an open access article published under a Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 1.56 MBLicence: CC BY

Cite this

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title = "Platinum catalysed hydrosilylation of propargylic alcohols",

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 {\ss}-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. ",

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AU - McAdam, Catherine A.

AU - McLaughlin, Mark G.

AU - Johnston, Adam J.S.

AU - Chen, Jun

AU - Walter, Magnus W.

AU - Cook, Matthew J.

PY - 2013/7/21

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N2 - 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 ß-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.

AB - 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 ß-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.

U2 - 10.1039/C3OB40496J

DO - 10.1039/C3OB40496J

M3 - Article

SN - 1477-0520

VL - 11

SP - 4488

EP - 4502

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 27

ER -

Platinum catalysed hydrosilylation of propargylic alcohols

Abstract

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