Issue 12, 2015
From the journal:

Chemical Communications

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

Roman Dobrovetsky,a   Katsuhiko Takeuchia  and  Douglas W. Stephan*ab  

* Corresponding authors

a Department of Chemistry, University of Toronto 80 St. George Street, Toronto, Ontario, Canada
E-mail: dstephan@chem.utoronto.ca
Web: http://www.chem.utoronto.ca/staff/DSTEPHAN

b Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia

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.

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

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Article information

DOI
https://doi.org/10.1039/C4CC09526J
Article type
Communication
Submitted
28 Nov 2014
Accepted
20 Dec 2014
First published
22 Dec 2014

Chem. Commun., 2015,51, 2396-2398

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

R. Dobrovetsky, K. Takeuchi and D. W. Stephan, Chem. Commun., 2015, 51, 2396 DOI: 10.1039/C4CC09526J

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