Syntheses of Phosphonium Salts from Phosphines and Carbenium: Efficient CO2 Fixation and Phase-Transfer Catalysts

Aslam C. Shaikh; José M. Veleta; Jan Bloch; Hannah J. Goodman; Thomas L. Gianetti

doi:10.1002/ejoc.202000221

Syntheses of Phosphonium Salts from Phosphines and Carbenium: Efficient CO₂ Fixation and Phase-Transfer Catalysts

Aslam C. Shaikh, José M. Veleta, Jan Bloch, Hannah J. Goodman, Thomas L. Gianetti

Chemistry and Biochemistry

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

4 Scopus citations

Abstract

A new library of phosphonium salts has been synthesized from the reaction of tris-(2,6-dimethoxyphenyl)carbenium with different phosphines. The resultant phosphoninum salts work as efficient phase-transfer catalysts for the alkylation of 1,3-dicarbonyl compounds. One compound, a bifunctional phosphonium salt prepared from tris-(2,6-dimethoxyphenyl)carbenium and an aminophosphine, was also found to be an efficient catalyst for CO₂ fixation reactions with epoxides under mild conditions.

Original language	English (US)
Pages (from-to)	2553-2559
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.202000221
State	Published - May 10 2020

Keywords

Bifunctional catalyst
CO2 fixation
Phase-transfer catalysis
Phosphonium
Triarylcarbenium

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.202000221

Cite this

@article{e2a1e608ad294b828dfc49a50b36af6e,

title = "Syntheses of Phosphonium Salts from Phosphines and Carbenium: Efficient CO2 Fixation and Phase-Transfer Catalysts",

abstract = "A new library of phosphonium salts has been synthesized from the reaction of tris-(2,6-dimethoxyphenyl)carbenium with different phosphines. The resultant phosphoninum salts work as efficient phase-transfer catalysts for the alkylation of 1,3-dicarbonyl compounds. One compound, a bifunctional phosphonium salt prepared from tris-(2,6-dimethoxyphenyl)carbenium and an aminophosphine, was also found to be an efficient catalyst for CO2 fixation reactions with epoxides under mild conditions.",

keywords = "Bifunctional catalyst, CO2 fixation, Phase-transfer catalysis, Phosphonium, Triarylcarbenium",

author = "Shaikh, {Aslam C.} and Veleta, {Jos{\'e} M.} and Jan Bloch and Goodman, {Hannah J.} and Gianetti, {Thomas L.}",

note = "Funding Information: Support has been provided by the Donors of the American Chemical Society Petroleum Research Fund (59631‐DNI3). Publisher Copyright: {\textcopyright} 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2020",

month = may,

day = "10",

doi = "10.1002/ejoc.202000221",

language = "English (US)",

volume = "2020",

pages = "2553--2559",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

number = "17",

}

TY - JOUR

T1 - Syntheses of Phosphonium Salts from Phosphines and Carbenium

T2 - Efficient CO2 Fixation and Phase-Transfer Catalysts

AU - Shaikh, Aslam C.

AU - Veleta, José M.

AU - Bloch, Jan

AU - Goodman, Hannah J.

AU - Gianetti, Thomas L.

N1 - Funding Information: Support has been provided by the Donors of the American Chemical Society Petroleum Research Fund (59631‐DNI3). Publisher Copyright: © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2020/5/10

Y1 - 2020/5/10

N2 - A new library of phosphonium salts has been synthesized from the reaction of tris-(2,6-dimethoxyphenyl)carbenium with different phosphines. The resultant phosphoninum salts work as efficient phase-transfer catalysts for the alkylation of 1,3-dicarbonyl compounds. One compound, a bifunctional phosphonium salt prepared from tris-(2,6-dimethoxyphenyl)carbenium and an aminophosphine, was also found to be an efficient catalyst for CO2 fixation reactions with epoxides under mild conditions.

AB - A new library of phosphonium salts has been synthesized from the reaction of tris-(2,6-dimethoxyphenyl)carbenium with different phosphines. The resultant phosphoninum salts work as efficient phase-transfer catalysts for the alkylation of 1,3-dicarbonyl compounds. One compound, a bifunctional phosphonium salt prepared from tris-(2,6-dimethoxyphenyl)carbenium and an aminophosphine, was also found to be an efficient catalyst for CO2 fixation reactions with epoxides under mild conditions.

KW - Bifunctional catalyst

KW - CO2 fixation

KW - Phase-transfer catalysis

KW - Phosphonium

KW - Triarylcarbenium

UR - http://www.scopus.com/inward/record.url?scp=85083966958&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85083966958&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202000221

DO - 10.1002/ejoc.202000221

M3 - Article

AN - SCOPUS:85083966958

SN - 1434-193X

VL - 2020

SP - 2553

EP - 2559

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 17

ER -

Syntheses of Phosphonium Salts from Phosphines and Carbenium: Efficient CO₂ Fixation and Phase-Transfer Catalysts

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 1984242: Experimental Crystal Structure Determination

Cite this

Syntheses of Phosphonium Salts from Phosphines and Carbenium: Efficient CO2 Fixation and Phase-Transfer Catalysts

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1984242: Experimental Crystal Structure Determination

Cite this

Syntheses of Phosphonium Salts from Phosphines and Carbenium: Efficient CO₂ Fixation and Phase-Transfer Catalysts