PtCl2/XPhos: A highly efficient and readily available catalyst for the hydrosilylation of propargylic alcohols

McLaughlin, Mark; Cook, Matthew J.

doi:10.1039/c1cc14433b

Cited by 46 publications

(20 citation statements)

References 28 publications

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“…Compounds 2a-2g, 2o, 4a-4d, 4e, 4j-4k and 4v were fully characterised and reported previously. 58 For the synthesis of the starting alkynes see the ESI. †…”

Section: Methodsmentioning

confidence: 99%

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Platinum catalysed hydrosilylation of propargylic alcohols

et al. 2013

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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.

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“…Compounds 2a-2g, 2o, 4a-4d, 4e, 4j-4k and 4v were fully characterised and reported previously. 58 For the synthesis of the starting alkynes see the ESI. †…”

Section: Methodsmentioning

confidence: 99%

“…We discovered that the PtCl 2 /XPhos catalyst system was very efficient for propargylic alcohols vida infra. 58 Under these conditions the catalyst loading could be lowered to 1 mol% and 0.5 mol% platinum(II) chloride for the secondary and tertiary propargylic alcohols, respectively.…”

Section: Introductionmentioning

confidence: 99%

Platinum catalysed hydrosilylation of propargylic alcohols

et al. 2013

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“…A similar influence of the silyl group on the addition of the SiH group to the C≡C in terminal and internal alkynes was previously reported. 64 , 71 , 72…”

Section: Resultsmentioning

confidence: 99%

Alkenyl-Functionalized Open-Cage Silsesquioxanes (RSiMe₂O)₃R′₇Si₇O₉: A Novel Class of Building Nanoblocks

et al. 2021

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Trifunctional incompletely condensed polyhedral oligomeric silsesquioxanes (RSiMe 2 O) 3 R′ 7 Si 7 O 9 ( IC-POSS s) are considered as intriguing building nanoblocks dedicated to constructing highly advanced organic–inorganic molecules and polymers. Up to now, they have been mainly obtained via hydrosilylation of olefins, while the hydrosilylation of the C≡C bonds has not been studied at all, despite the enormous potential of this approach resulting from the possibility of introducing 3, 6, or even more functional groups into the IC-POSS structure. Therefore, in this work, we present a highly selective and efficient synthesis of the first example of tripodal alkenyl-functionalized IC-POSS s, obtained via platinum-catalyzed hydrosilylation of the terminal and internal alkynes, as well as symmetrically and nonsymmetrically 1,4-disubstituted buta-1,3-diynes with silsesquioxanes (HSiMe 2 O) 3 R′ 7 Si 7 O 9 (R′ = i -C 4 H 9 ( 1a ), (H 3 C) 3 CH 2 C(H 3 C)HCH 2 C ( 1b )). The resulting products are synthetic intermediates that contain C=C bonds and functional groups (e.g., OSiMe 3 , SiR 3 , Br, F, B(O(C(CH 3 ) 2 ) 2 (Bpin)), thienyl), which make them suitable for application in the synthesis of novel, complex, hybrid materials with unique properties.

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“…16 The latter system has also recently been found to functionalise a wide range of secondary and tertiary propargylic alcohols with exclusive regioselectivity for the b-(E)-vinylsilane products using a variety of silanes. 17 Mechanistically, platinum(II) and platinum(IV) species are believed to be reduced in situ by the silane to the catalytically active platinum(0) oxidation state.…”

Section: Trans-12-disubstituted Vinylsilanesmentioning

confidence: 99%

Synthesis of Vinylsilanes

Lim¹,

Anderson²

2012

Synthesis

116

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PtCl2/XPhos: A highly efficient and readily available catalyst for the hydrosilylation of propargylic alcohols

Abstract: A highly regioselective hydrosilylation of propargylic alcohols has been developed using an in situ prepared PtCl(2)/XPhos catalyst system. The reaction is tolerant of many functional groups and exhibits excellent regio and geometric selectivity.

Cited by 46 publications

References 28 publications

Platinum catalysed hydrosilylation of propargylic alcohols

Platinum catalysed hydrosilylation of propargylic alcohols

Alkenyl-Functionalized Open-Cage Silsesquioxanes (RSiMe₂O)₃R′₇Si₇O₉: A Novel Class of Building Nanoblocks

Synthesis of Vinylsilanes

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PtCl2/XPhos: A highly efficient and readily available catalyst for the hydrosilylation of propargylic alcohols

Abstract: A highly regioselective hydrosilylation of propargylic alcohols has been developed using an in situ prepared PtCl(2)/XPhos catalyst system. The reaction is tolerant of many functional groups and exhibits excellent regio and geometric selectivity.

Cited by 46 publications

References 28 publications

Platinum catalysed hydrosilylation of propargylic alcohols

Platinum catalysed hydrosilylation of propargylic alcohols

Alkenyl-Functionalized Open-Cage Silsesquioxanes (RSiMe2O)3R′7Si7O9: A Novel Class of Building Nanoblocks

Synthesis of Vinylsilanes

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Product

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About

Alkenyl-Functionalized Open-Cage Silsesquioxanes (RSiMe₂O)₃R′₇Si₇O₉: A Novel Class of Building Nanoblocks