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

[61] Beyond Aresta's complex:: Ni- and Pd-catalyzed organozinc coupling with CO2 [J].

Yeung, Charles S. ;

Dong, Vy M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (25) :7826-+

[62] Synthesis of Oxazolidinones by Efficient Fixation of Atmospheric CO2 with Propargylic Amines by using a Silver/1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) Dual-Catalyst System [J].

Yoshida, Masahiro ;

Mizuguchi, Tomotaka ;

Shishido, Kozo .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (49) :15578-15581

[63] Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by Poly(N-Heterocyclic Carbene)-Supported Silver Nanoparticles [J].

Yu, Dingyi ;

Tan, Mei Xuan ;

Zhang, Yugen .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) :969-974

[64] Copper- and copper-N-heterocyclic carbene-catalyzed C-H activating carboxylation of terminal alkynes with CO2 at ambient conditions [J].

Yu, Dingyi ;

Zhang, Yugen .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (47) :20184-20189

[65] The role of Mn doping in CeO2 for catalytic synthesis of aliphatic carbamate from CO2 [J].

Zhang, Ran ;

Guo, Li ;

Chen, Chen ;

Chen, Jizhong ;

Chen, Angjun ;

Zhao, Xiuge ;

Liu, Xuerui ;

Xiu, Yuhe ;

Hou, Zhenshan .

CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (05) :2959-2972

[66] Cu(I)-Catalyzed Carboxylative Coupling of Terminal Alkynes, Allylic Chlorides, and CO2 [J].

Zhang, Wen-Zhen ;

Li, Wen-Jie ;

Zhang, Xiao ;

Zhou, Hui ;

Lu, Xiao-Bing .

ORGANIC LETTERS, 2010, 12 (21) :4748-4751

[67] Ligand-free Ag(I)-catalyzed carboxylative coupling of terminal alkynes, chloride compounds, and CO2 [J].

Zhang, Xiao ;

Zhang, Wen-Zhen ;

Shi, Ling-Long ;

Zhu, Chuang ;

Jiang, Jiao-Lai ;

Lu, Xiao-Bing .

TETRAHEDRON, 2012, 68 (44) :9085-9089

[68] Silver(I)-catalyzed carboxylation of arylboronic esters with CO2 [J].

Zhang, Xiao ;

Zhang, Wen-Zhen ;

Shi, Ling-Long ;

Guo, Chun-Xiao ;

Zhang, Ling-Ling ;

Lu, Xiao-Bing .

CHEMICAL COMMUNICATIONS, 2012, 48 (50) :6292-6294

[69] Ligand-Free Ag(I)-Catalyzed Carboxylation of Terminal Alkynes with CO2 [J].

Zhang, Xiao ;

Zhang, Wen-Zhen ;

Ren, Xiang ;

Zhang, Lin-Lin ;

Lu, Xiao-Bing .

ORGANIC LETTERS, 2011, 13 (09) :2402-2405

[70] CO2 adducts of N-heterocyclic carbenes:: Thermal stability and catalytic activity toward the coupling of CO2 with epoxides [J].

Zhou, Hui ;

Zhang, Wen-Zhen ;

Liu, Cui-Hua ;

Qu, Jing-Ping ;

Lu, Xiao-Bing .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) :8039-8044

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