Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by an In Situ Ag2O/N-Heterocyclic Carbene Precursor System

Ye Yuan, Cheng Chen, Cheng Zeng, Bibimaryam Mousavi, Somboon Chaemchuen, Francis Verpoort

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A carboxylation of terminal alkynes with carbon dioxide (CO2) at ambient conditions was developed in situ using a series of N-heterocyclic carbene (NHC) precursors and Ag2O. The unique structure of NHCs largely increases the solubility of active Ag species and meanwhile activates CO2 by forming the NHC–CO2 adduct. This novel catalytic system demonstrated quite low Ag loading, very high activities, wide substrate generality and excellent tolerance for a variety of functionalities. In addition, avoiding cumbersome synthesis procedures, processing, and reserving of the photosensitive Ag complex, this system could be stored and operated as straightforward as the inorganic Ag salt catalysts.

Original languageEnglish
Pages (from-to)882-887
Number of pages6
JournalChemCatChem
Volume9
Issue number5
DOIs
Publication statusPublished - 8 Mar 2017

Fingerprint

carboxylation
Carboxylation
Alkynes
carbenes
alkynes
complex systems
Carbon Dioxide
adducts
carbon dioxide
Large scale systems
Carbon dioxide
solubility
Solubility
Salts
salts
catalysts
Catalysts
Substrates
synthesis
Processing

Keywords

  • alkynes
  • carbenes
  • carboxylation
  • reaction mechanisms
  • silver

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by an In Situ Ag2O/N-Heterocyclic Carbene Precursor System. / Yuan, Ye; Chen, Cheng; Zeng, Cheng; Mousavi, Bibimaryam; Chaemchuen, Somboon; Verpoort, Francis.

In: ChemCatChem, Vol. 9, No. 5, 08.03.2017, p. 882-887.

Research output: Contribution to journalArticle

Yuan, Ye ; Chen, Cheng ; Zeng, Cheng ; Mousavi, Bibimaryam ; Chaemchuen, Somboon ; Verpoort, Francis. / Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by an In Situ Ag2O/N-Heterocyclic Carbene Precursor System. In: ChemCatChem. 2017 ; Vol. 9, No. 5. pp. 882-887.
@article{fb1ad136694149f5a913a930ae9bbd1b,
title = "Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by an In Situ Ag2O/N-Heterocyclic Carbene Precursor System",
abstract = "A carboxylation of terminal alkynes with carbon dioxide (CO2) at ambient conditions was developed in situ using a series of N-heterocyclic carbene (NHC) precursors and Ag2O. The unique structure of NHCs largely increases the solubility of active Ag species and meanwhile activates CO2 by forming the NHC–CO2 adduct. This novel catalytic system demonstrated quite low Ag loading, very high activities, wide substrate generality and excellent tolerance for a variety of functionalities. In addition, avoiding cumbersome synthesis procedures, processing, and reserving of the photosensitive Ag complex, this system could be stored and operated as straightforward as the inorganic Ag salt catalysts.",
keywords = "alkynes, carbenes, carboxylation, reaction mechanisms, silver",
author = "Ye Yuan and Cheng Chen and Cheng Zeng and Bibimaryam Mousavi and Somboon Chaemchuen and Francis Verpoort",
year = "2017",
month = "3",
day = "8",
doi = "10.1002/cctc.201601379",
language = "English",
volume = "9",
pages = "882--887",
journal = "ChemCatChem",
issn = "1867-3880",
publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",
number = "5",

}

TY - JOUR

T1 - Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by an In Situ Ag2O/N-Heterocyclic Carbene Precursor System

AU - Yuan, Ye

AU - Chen, Cheng

AU - Zeng, Cheng

AU - Mousavi, Bibimaryam

AU - Chaemchuen, Somboon

AU - Verpoort, Francis

PY - 2017/3/8

Y1 - 2017/3/8

N2 - A carboxylation of terminal alkynes with carbon dioxide (CO2) at ambient conditions was developed in situ using a series of N-heterocyclic carbene (NHC) precursors and Ag2O. The unique structure of NHCs largely increases the solubility of active Ag species and meanwhile activates CO2 by forming the NHC–CO2 adduct. This novel catalytic system demonstrated quite low Ag loading, very high activities, wide substrate generality and excellent tolerance for a variety of functionalities. In addition, avoiding cumbersome synthesis procedures, processing, and reserving of the photosensitive Ag complex, this system could be stored and operated as straightforward as the inorganic Ag salt catalysts.

AB - A carboxylation of terminal alkynes with carbon dioxide (CO2) at ambient conditions was developed in situ using a series of N-heterocyclic carbene (NHC) precursors and Ag2O. The unique structure of NHCs largely increases the solubility of active Ag species and meanwhile activates CO2 by forming the NHC–CO2 adduct. This novel catalytic system demonstrated quite low Ag loading, very high activities, wide substrate generality and excellent tolerance for a variety of functionalities. In addition, avoiding cumbersome synthesis procedures, processing, and reserving of the photosensitive Ag complex, this system could be stored and operated as straightforward as the inorganic Ag salt catalysts.

KW - alkynes

KW - carbenes

KW - carboxylation

KW - reaction mechanisms

KW - silver

UR - http://www.scopus.com/inward/record.url?scp=85013481349&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85013481349&partnerID=8YFLogxK

U2 - 10.1002/cctc.201601379

DO - 10.1002/cctc.201601379

M3 - Article

VL - 9

SP - 882

EP - 887

JO - ChemCatChem

JF - ChemCatChem

SN - 1867-3880

IS - 5

ER -