The First Ring-Expanded NHC-Copper(I) Phosphides as Catalysts in the Highly Selective Hydrophosphination of Isocyanates

Thomas Horsley Downie, Jonathan Hall, Thomas Collier Finn, David Liptrot, John Lowe, Mary Mahon, Claire McMullin, Michael Whittlesey

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31 Citations (SciVal)

Abstract

A range of N-heterocyclic carbene-supported copper diphenylphosphides (NHC = IPr, 6-Dipp, SIMes and 6-Mes) were synthesised. These include the first reports of ring-expanded NHC-copper(i) phosphides. The compounds were characterised by NMR spectroscopy and X-ray crystallography. Reaction of (6-Dipp)CuPPh2 with isocyanates, isothiocyanates and carbon disulfide results in the insertion of the heterocumulene into the Cu-P bond. The NHC-copper phosphides were found to be the most selective catalysts yet reported for the hydrophosphination of isocyanates. They provide access to a broad range of phosphinocarboxamides in excellent conversion and good yield.
Original languageEnglish
Pages (from-to)13359-13362
Number of pages4
JournalChemical Communications
Volume56
Issue number87
Early online date1 Oct 2020
DOIs
Publication statusPublished - 11 Nov 2020

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