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

被引：48

作者：

Yuan, Ye ^{[1
,2
]}

Chen, Cheng ^{[1
]}

Zeng, Cheng ^{[2
]}

Mousavi, Bibimaryam ^{[1
]}

Chaemchuen, Somboon ^{[1
]}

Verpoort, Francis ^{[1
,2
,3
,4
]}

机构：

[1] Wuhan Univ Technol, State Key Lab Adv Technol Mat Synth & Proc, Wuhan 430070, Peoples R China

[2] Wuhan Univ Technol, Sch Mat Sci & Engn, Wuhan 430070, Peoples R China

[3] Natl Res Tomsk Polytech Univ, Lenin Ave 30, Tomsk 634050, Russia

[4] Univ Ghent, Global Campus Songdo, Incheon, South Korea

来源：

CHEMCATCHEM | 2017年 / 9卷 / 05期

基金：

高等学校博士学科点专项科研基金;

关键词：

alkynes; carbenes; carboxylation; reaction mechanisms; silver; ALKENYLBORONIC ESTERS; EFFICIENT CATALYSTS; PROPARGYLIC AMINES; AMBIENT CONDITIONS; CYCLIC CARBONATES; IONIC LIQUIDS; CO2; SILVER; COMPLEXES; DERIVATIVES;

D O I：

10.1002/cctc.201601379

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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.

引用

页码：882 / 887

页数：6

共 70 条

[1]

[Anonymous], ANGEW CHEM

[2] C?H Carboxylation of Terminal Alkynes Catalyzed by Low Loadings of Silver(I)/DMSO at Ambient CO2 Pressure [J].

Arndt, Matthias ;

Risto, Eugen ;

Krause, Thilo ;

Goossen, Lukas J. .

CHEMCATCHEM, 2012, 4 (04) :484-487

[3] Sulfonated Water-Soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-Transfer Agents to Platinum(II) [J].

Baquero, Edwin A. ;

Silbestri, Gustavo F. ;

Gomez-Sal, Pilar ;

Flores, Juan C. ;

de Jesus, Ernesto .

ORGANOMETALLICS, 2013, 32 (09) :2814-2826

[4] CARBOXYLATION OF ACTIVE METHYLENE-COMPOUNDS USING ANILIDE, POTASSIUM CARBONATE, AND CARBON-DIOXIDE [J].

CHIBA, K ;

TAGAYA, H ;

KARASU, M ;

ISHIZUKA, M ;

SUGO, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (02) :452-454

[5] THE CARBOXYLATION OF ACTIVE METHYLENE-COMPOUNDS WITH CARBON-DIOXIDE IN THE PRESENCE OF 18-CROWN-6 AND POTASSIUM CARBONATE [J].

CHIBA, K ;

TAGAYA, H ;

MIURA, S ;

KARASU, M .

CHEMISTRY LETTERS, 1992, (06) :923-926

[6]

Cokoja M., 2011, ANGEW CHEM, V123, P8662, DOI DOI 10.1002/ANGE.201102010

[7] Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? [J].

Cokoja, Mirza ;

Bruckmeier, Christian ;

Rieger, Bernhard ;

Herrmann, Wolfgang A. ;

Kuehn, Fritz E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8510-8537

[8] Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings [J].

Comerford, James W. ;

Ingram, Ian D. V. ;

North, Michael ;

Wu, Xiao .

GREEN CHEMISTRY, 2015, 17 (04) :1966-1987

[9] Synthesis, structure and emission properties of spirocyclic benzofuranones and dihydroindolones:: A domino insertion-coupling-isomerization-Diels-Alder approach to rigid fluorophores [J].

D'Souza, Daniel M. ;

Kiel, Alexander ;

Herten, Dirk-Peter ;

Rominger, Frank ;

Mueller, Thomas J. J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (02) :529-547

[10] Silver-catalyzed one-pot synthesis of arylnaphthalene lactones [J].

Eghbali, Nicolas ;

Eddy, Jennifer ;

Anastas, Paul T. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6932-6935

← 1 2 3 4 5 6 7 →