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

11 Citations (SciVal)

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
Publication status	Published - 15 Jul 2022

Bibliographical 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

Keywords

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

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1021/acscatal.2c02199Licence: CC BY

Cite this

@article{ee337266c57748ee93f38037259da94c,

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 ",

year = "2022",

month = jul,

day = "15",

doi = "10.1021/acscatal.2c02199",

language = "English",

volume = "12",

pages = "8214--8219",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=85135590256&partnerID=8YFLogxK

U2 - 10.1021/acscatal.2c02199

DO - 10.1021/acscatal.2c02199

M3 - Article

AN - SCOPUS:85135590256

SN - 2155-5435

VL - 12

SP - 8214

EP - 8219

JO - ACS Catalysis

JF - ACS Catalysis

IS - 14

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this