A Copper(I) Platform for One-Pot P-H Bond Formation and Hydrophosphination of Heterocumulenes

Thomas M. Horsley Downie; Mary F. Mahon; John P. Lowe; Rowan M. Bailey; David J. Liptrot

doi:10.1021/acscatal.2c02199

A Copper(I) Platform for One-Pot P-H Bond Formation and Hydrophosphination of Heterocumulenes

Thomas M. Horsley Downie, Mary F. Mahon, John P. Lowe, Rowan M. Bailey, David J. Liptrot

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

Abstract

The reaction of phosphorus(III) esters with pinacolborane generates phosphines via the action of an NHC-copper(I) catalyst. This gives access, within minutes, to 12 P–H bonded species, including secondary and primary phosphines as well as PH3, in excellent conversions. These phosphines can be subsequently applied in the copper(I)-catalyzed hydrophosphination of heterocumulenes in a telescoped, one-pot fashion. This approach yielded 12 phosphaureas, 3 phosphaguanidines, and 2 phosphathioureas in moderate to excellent yields without the need to handle toxic, pyrophoric, or gaseous P–H bond containing compounds. The crystal structures of two of the phosphaureas, PhP(C(O)NHPh)2 and P(C(O)NHPh)3, are presented.

Original language	English
Pages (from-to)	8214-8219
Number of pages	6
Journal	ACS Catalysis
Volume	12
Issue number	14
Early online date	24 Jun 2022
DOIs	https://doi.org/10.1021/acscatal.2c02199 https://doi.org/10.1021/acscatal.2c02199
Publication status	Published - 15 Jul 2022

Keywords

copper catalysis
heterocumulene
homogeneous catalysis
hydrophosphination
P-H bond formation
phosphine

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1021/acscatal.2c02199

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title = "A Copper(I) Platform for One-Pot P-H Bond Formation and Hydrophosphination of Heterocumulenes",

abstract = "The reaction of phosphorus(III) esters with pinacolborane generates phosphines via the action of an NHC-copper(I) catalyst. This gives access, within minutes, to 12 P–H bonded species, including secondary and primary phosphines as well as PH3, in excellent conversions. These phosphines can be subsequently applied in the copper(I)-catalyzed hydrophosphination of heterocumulenes in a telescoped, one-pot fashion. This approach yielded 12 phosphaureas, 3 phosphaguanidines, and 2 phosphathioureas in moderate to excellent yields without the need to handle toxic, pyrophoric, or gaseous P–H bond containing compounds. The crystal structures of two of the phosphaureas, PhP(C(O)NHPh)2 and P(C(O)NHPh)3, are presented.",

keywords = "copper catalysis, heterocumulene, homogeneous catalysis, hydrophosphination, P-H bond formation, phosphine",

author = "{Horsley Downie}, {Thomas M.} and Mahon, {Mary F.} and Lowe, {John P.} and Bailey, {Rowan M.} and Liptrot, {David J.}",

note = "Funding Information: D.J.L. thanks the Royal Society for the support of a University Research Fellowship. We wish to thank the EPSRC for funding and the University of Bath and MC for use of their analysis facilities. We thank the EPSRC UK National Crystallography Service at the University of Southampton for the collection of the crystallographic data for 2o . 2 ",

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doi = "10.1021/acscatal.2c02199",

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T1 - A Copper(I) Platform for One-Pot P-H Bond Formation and Hydrophosphination of Heterocumulenes

AU - Horsley Downie, Thomas M.

AU - Mahon, Mary F.

AU - Lowe, John P.

AU - Bailey, Rowan M.

AU - Liptrot, David J.

N1 - Funding Information: D.J.L. thanks the Royal Society for the support of a University Research Fellowship. We wish to thank the EPSRC for funding and the University of Bath and MC for use of their analysis facilities. We thank the EPSRC UK National Crystallography Service at the University of Southampton for the collection of the crystallographic data for 2o . 2

PY - 2022/7/15

Y1 - 2022/7/15

N2 - The reaction of phosphorus(III) esters with pinacolborane generates phosphines via the action of an NHC-copper(I) catalyst. This gives access, within minutes, to 12 P–H bonded species, including secondary and primary phosphines as well as PH3, in excellent conversions. These phosphines can be subsequently applied in the copper(I)-catalyzed hydrophosphination of heterocumulenes in a telescoped, one-pot fashion. This approach yielded 12 phosphaureas, 3 phosphaguanidines, and 2 phosphathioureas in moderate to excellent yields without the need to handle toxic, pyrophoric, or gaseous P–H bond containing compounds. The crystal structures of two of the phosphaureas, PhP(C(O)NHPh)2 and P(C(O)NHPh)3, are presented.

AB - The reaction of phosphorus(III) esters with pinacolborane generates phosphines via the action of an NHC-copper(I) catalyst. This gives access, within minutes, to 12 P–H bonded species, including secondary and primary phosphines as well as PH3, in excellent conversions. These phosphines can be subsequently applied in the copper(I)-catalyzed hydrophosphination of heterocumulenes in a telescoped, one-pot fashion. This approach yielded 12 phosphaureas, 3 phosphaguanidines, and 2 phosphathioureas in moderate to excellent yields without the need to handle toxic, pyrophoric, or gaseous P–H bond containing compounds. The crystal structures of two of the phosphaureas, PhP(C(O)NHPh)2 and P(C(O)NHPh)3, are presented.

KW - copper catalysis

KW - heterocumulene

KW - homogeneous catalysis

KW - hydrophosphination

KW - P-H bond formation

KW - phosphine

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DO - 10.1021/acscatal.2c02199

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SP - 8214

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JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

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ER -

A Copper(I) Platform for One-Pot P-H Bond Formation and Hydrophosphination of Heterocumulenes

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Keywords

ASJC Scopus subject areas

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