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.]",

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

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

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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

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DO - 10.1007/s10562-016-1920-5

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SP - 463

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JO - Catalysis Letters

JF - Catalysis Letters

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

Abstract

Keywords

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