Metal-free Lewis acid mediated dehydrocoupling of phosphines and concurrent hydrogenation

Roman Dobrovetsky; Katsuhiko Takeuchi; Douglas W. Stephan

doi:10.1039/c4cc09526j

Metal-free Lewis acid mediated dehydrocoupling of phosphines and concurrent hydrogenation

Roman Dobrovetsky, Katsuhiko Takeuchi, Douglas W. Stephan^*

^*Corresponding author for this work

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

32 Scopus citations

Abstract

The stoichiometric reaction of trityl cation with two equivalents of Ph₂PH affords the phosphine stabilized phosphenium salt [Ph₂(H)PPPh₂][B(C₆F₅)₄] via hydride abstraction, while catalytic amounts of B(p-HC₆F₄)₃ effects catalytic phosphine dehydrocoupling with the liberation of H₂. This reaction is accelerated by the presence of olefin or imine, effecting concurrent hydrogenation.

Original language	English
Pages (from-to)	2396-2398
Number of pages	3
Journal	Chemical Communications
Volume	51
Issue number	12
DOIs	https://doi.org/10.1039/c4cc09526j
State	Published - 11 Feb 2015
Externally published	Yes

Funding

Funders	Funder number
Natural Sciences and Engineering Research Council of Canada

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abstract = "The stoichiometric reaction of trityl cation with two equivalents of Ph2PH affords the phosphine stabilized phosphenium salt [Ph2(H)PPPh2][B(C6F5)4] via hydride abstraction, while catalytic amounts of B(p-HC6F4)3 effects catalytic phosphine dehydrocoupling with the liberation of H2. This reaction is accelerated by the presence of olefin or imine, effecting concurrent hydrogenation.",

author = "Roman Dobrovetsky and Katsuhiko Takeuchi and Stephan, {Douglas W.}",

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N2 - The stoichiometric reaction of trityl cation with two equivalents of Ph2PH affords the phosphine stabilized phosphenium salt [Ph2(H)PPPh2][B(C6F5)4] via hydride abstraction, while catalytic amounts of B(p-HC6F4)3 effects catalytic phosphine dehydrocoupling with the liberation of H2. This reaction is accelerated by the presence of olefin or imine, effecting concurrent hydrogenation.

AB - The stoichiometric reaction of trityl cation with two equivalents of Ph2PH affords the phosphine stabilized phosphenium salt [Ph2(H)PPPh2][B(C6F5)4] via hydride abstraction, while catalytic amounts of B(p-HC6F4)3 effects catalytic phosphine dehydrocoupling with the liberation of H2. This reaction is accelerated by the presence of olefin or imine, effecting concurrent hydrogenation.

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Metal-free Lewis acid mediated dehydrocoupling of phosphines and concurrent hydrogenation

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