The first ring-expanded NHC–copper(i) phosphides as catalysts in the highly selective hydrophosphination of isocyanates

Thomas M. Horsley Downie; Jonathan W. Hall; Thomas P. Collier Finn; David J. Liptrot; John P. Lowe; Mary F. Mahon; Claire L. McMullin; Michael K. Whittlesey

doi:10.1039/D0CC05694D

The first ring-expanded NHC–copper(i) phosphides as catalysts in the highly selective hydrophosphination of isocyanates

Thomas M. Horsley Downie, Jonathan W. Hall, Thomas P. Collier Finn, David J. Liptrot, John P. Lowe, Mary F. Mahon, Claire L. McMullin, Michael K. Whittlesey

Pure And Applied Chemistry

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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.

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 - 31 Dec 2020

Funding

We acknowledge financial support from the EPSRC Centre for Doctoral Training in Catalysis (EP/L016443/1) for JWH

Keywords

phosphinocarboxamides
organophosphorus compounds

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10.1039/D0CC05694DLicence: CC BY-NC 3.0

Horsley-Downie-etal-CC-2020-The-first-ring-expanded-NHC-copper-i-phosphidesFinal published version, 1.95 MBLicence: CC BY-NC 3.0

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title = "The first ring-expanded NHC–copper(i) phosphides as catalysts in the highly selective hydrophosphination of isocyanates",

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.",

keywords = "phosphinocarboxamides, organophosphorus compounds",

author = "{Horsley Downie}, {Thomas M.} and Hall, {Jonathan W.} and {Collier Finn}, {Thomas P.} and Liptrot, {David J.} and Lowe, {John P.} and Mahon, {Mary F.} and McMullin, {Claire L.} and Whittlesey, {Michael K.}",

year = "2020",

month = dec,

day = "31",

doi = "10.1039/D0CC05694D",

language = "English",

volume = "56",

pages = "13359--13362",

journal = "Chemical Communications",

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TY - JOUR

T1 - The first ring-expanded NHC–copper(i) phosphides as catalysts in the highly selective hydrophosphination of isocyanates

AU - Horsley Downie, Thomas M.

AU - Hall, Jonathan W.

AU - Collier Finn, Thomas P.

AU - Liptrot, David J.

AU - Lowe, John P.

AU - Mahon, Mary F.

AU - McMullin, Claire L.

AU - Whittlesey, Michael K.

PY - 2020/12/31

Y1 - 2020/12/31

N2 - 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.

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.

KW - phosphinocarboxamides

KW - organophosphorus compounds

U2 - 10.1039/D0CC05694D

DO - 10.1039/D0CC05694D

M3 - Article

SN - 1359-7345

VL - 56

SP - 13359

EP - 13362

JO - Chemical Communications

JF - Chemical Communications

IS - 87

ER -

The first ring-expanded NHC–copper(i) phosphides as catalysts in the highly selective hydrophosphination of isocyanates

Abstract

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Keywords

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