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

doi:10.1039/D0CC05694D

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

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

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 language	English
Pages (from-to)	13359-13362
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	87
Early online date	1 Oct 2020
DOIs	https://doi.org/10.1039/D0CC05694D
Publication status	Published - 11 Nov 2020

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The First Ring-Expanded NHC-Copper(I) Phosphides as Catalysts in the Highly Selective Hydrophosphination of Isocyanates. / Horsley Downie, Thomas ; Hall, Jonathan; Collier Finn, Thomas; Liptrot, David; Lowe, John; Mahon, Mary ; McMullin, Claire ; Whittlesey, Michael.

In: Chemical Communications, Vol. 56, No. 87, 11.11.2020, p. 13359-13362.

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

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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.",

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AU - McMullin, Claire

AU - Whittlesey, Michael

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AB - 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.

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