Inserting CO2 into Terminal Alkynes via Bis-(NHC)-Metal Complexes

Matthias Vandichel; Heriberto Díaz Velázquez; Zhao Xuan Wu; Francis Verpoort

doi:10.1007/s10562-016-1920-5

Inserting CO2 into Terminal Alkynes via Bis-(NHC)-Metal Complexes

Matthias Vandichel
, Heriberto Díaz Velázquez
, Zhao Xuan Wu
, Francis Verpoort

Department of Chemical Sciences

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

Abstract

Abstract: The direct interaction between CO₂and terminal alkynes in the presence of bis-(NHC)-metal catalysts at ambient conditions was studied. Two Cu and Ag-based bis-N-heterocyclic carbene Transition Metal catalysts were synthesized. The (NHC)₂-Ag complex showed a better catalytic performance towards the carboxylation of terminal alkynes in comparison with the copper analogue even for the conversion of acetylene gas. The optimized conditions for the carboxylation are: the use of Cs₂CO₃as additive, one atmosphere CO₂and room temperature using 1% mol catalyst. Mechanistic insight into the reaction mechanism is obtained by means of state-of-the-art first principles calculations. Graphical Abstract: [Figure not available: see fulltext.]

Original language	English (Ireland)
Pages (from-to)	463-471
Number of pages	9
Journal	Catalysis Letters
Volume	147
Issue number	2
DOIs	https://doi.org/10.1007/s10562-016-1920-5 https://doi.org/10.1007/s10562-016-1920-5
Publication status	Published - Feb 2017

Keywords

Carboxylation
DFT
Homogeneous catalysis
N-Heterocyclic carbene
Terminal alkyne

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title = "Inserting CO2 into Terminal Alkynes via Bis-(NHC)-Metal Complexes",

abstract = "Abstract: The direct interaction between CO2and terminal alkynes in the presence of bis-(NHC)-metal catalysts at ambient conditions was studied. Two Cu and Ag-based bis-N-heterocyclic carbene Transition Metal catalysts were synthesized. The (NHC)2-Ag complex showed a better catalytic performance towards the carboxylation of terminal alkynes in comparison with the copper analogue even for the conversion of acetylene gas. The optimized conditions for the carboxylation are: the use of Cs2CO3as additive, one atmosphere CO2and room temperature using 1\% mol catalyst. Mechanistic insight into the reaction mechanism is obtained by means of state-of-the-art first principles calculations. Graphical Abstract: [Figure not available: see fulltext.]",

keywords = "Carboxylation, DFT, Homogeneous catalysis, N-Heterocyclic carbene, Terminal alkyne",

author = "Matthias Vandichel and \{D{\'i}az Vel{\'a}zquez\}, Heriberto and Wu, \{Zhao Xuan\} and Francis Verpoort",

note = "Publisher Copyright: {\textcopyright} 2017, Springer Science+Business Media New York.",

year = "2017",

month = feb,

doi = "10.1007/s10562-016-1920-5",

language = "English (Ireland)",

volume = "147",

pages = "463--471",

journal = "Catalysis Letters",

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TY - JOUR

T1 - Inserting CO2 into Terminal Alkynes via Bis-(NHC)-Metal Complexes

AU - Vandichel, Matthias

AU - Díaz Velázquez, Heriberto

AU - Wu, Zhao Xuan

AU - Verpoort, Francis

PY - 2017/2

Y1 - 2017/2

N2 - Abstract: The direct interaction between CO2and terminal alkynes in the presence of bis-(NHC)-metal catalysts at ambient conditions was studied. Two Cu and Ag-based bis-N-heterocyclic carbene Transition Metal catalysts were synthesized. The (NHC)2-Ag complex showed a better catalytic performance towards the carboxylation of terminal alkynes in comparison with the copper analogue even for the conversion of acetylene gas. The optimized conditions for the carboxylation are: the use of Cs2CO3as additive, one atmosphere CO2and room temperature using 1% mol catalyst. Mechanistic insight into the reaction mechanism is obtained by means of state-of-the-art first principles calculations. Graphical Abstract: [Figure not available: see fulltext.]

AB - Abstract: The direct interaction between CO2and terminal alkynes in the presence of bis-(NHC)-metal catalysts at ambient conditions was studied. Two Cu and Ag-based bis-N-heterocyclic carbene Transition Metal catalysts were synthesized. The (NHC)2-Ag complex showed a better catalytic performance towards the carboxylation of terminal alkynes in comparison with the copper analogue even for the conversion of acetylene gas. The optimized conditions for the carboxylation are: the use of Cs2CO3as additive, one atmosphere CO2and room temperature using 1% mol catalyst. Mechanistic insight into the reaction mechanism is obtained by means of state-of-the-art first principles calculations. Graphical Abstract: [Figure not available: see fulltext.]

KW - Carboxylation

KW - DFT

KW - Homogeneous catalysis

KW - N-Heterocyclic carbene

KW - Terminal alkyne

UR - https://www.scopus.com/pages/publications/85009493270

U2 - 10.1007/s10562-016-1920-5

DO - 10.1007/s10562-016-1920-5

M3 - Article

AN - SCOPUS:85009493270

SN - 1011-372X

VL - 147

SP - 463

EP - 471

JO - Catalysis Letters

JF - Catalysis Letters

IS - 2

ER -

Inserting CO2 into Terminal Alkynes via Bis-(NHC)-Metal Complexes

Abstract

Keywords

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