Transition metal-free carboxylation of terminal alkynes with carbon dioxide through dual activation: Synthesis of propiolic acids

被引：15

作者：

Wang, Wan-Hui ^{[1
,2
]}

Feng, Xiujuan ^{[1
]}

Sui, Kun ^{[1
,2
]}

Fang, Dingqiao ^{[1
]}

Bao, Ming ^{[1
,2
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116023, Peoples R China

[2] Dalian Univ Technol, Sch Petr & Chem Engn, Panjin 124221, Peoples R China

来源：

JOURNAL OF CO2 UTILIZATION | 2019年 / 32卷

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

Carboxylation; CO2; utilization; Organic salt; Dual activation; Propiolic acid; CATALYZED CARBOXYLATION; CO2; HYDROGENATION; CHLORIDES;

D O I：

10.1016/j.jcou.2019.04.011

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The combination use of quaternary ammonium salt and inorganic base in low-boiling-point solvent is presented as a new strategy for terminal alkyne carboxylation with CO2. The carboxylation of terminal alkyne with CO2 proceeded smoothly in the presence of tetra-n-butylammonium acetate and K2CO3 through dual activation under relatively mild conditions to produce the corresponding propiolic acids in satisfactory to excellent yields.

引用

页码：140 / 145

页数：6

共 35 条

[1] Transition-Metal-Catalyzed Carboxylation of C-H Bonds
Ackermann, Lutz
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) : 3842 - 3844
[2] C?H Carboxylation of Terminal Alkynes Catalyzed by Low Loadings of Silver(I)/DMSO at Ambient CO2 Pressure
Arndt, Matthias
Risto, Eugen
Krause, Thilo
Goossen, Lukas J.
[J]. CHEMCATCHEM, 2012, 4 (04) : 484 - 487
[3] Copper(0) Nanoparticles Supported on Al2O3 as Catalyst for Carboxylation of Terminal Alkynes
Bondarenko, Grigoriy N.
Dvurechenskaya, Ekaterina G.
Magommedov, Eldar Sh.
Beletskaya, Irina P.
[J]. CATALYSIS LETTERS, 2017, 147 (10) : 2570 - 2580
[4] Direct C-H carboxylation with complexes of the coinage metals
Boogaerts, Ine I. F.
Nolan, Steven P.
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (11) : 3021 - 3024
[5] CuCl2@Poly-IL catalyzed carboxylation of terminal alkynes through CO2 utilization
Chaugule, Avinash A.
Tamboli, Ashif H.
Kim, Hern
[J]. CHEMICAL ENGINEERING JOURNAL, 2017, 326 : 1009 - 1019
[6] Carboxylation of terminal alkynes with CO2 catalyzed by bis(amidate) rare-earth metal amides
Cheng, Hao
Zhao, Bei
Yao, Yingming
Lu, Chengrong
[J]. GREEN CHEMISTRY, 2015, 17 (03) : 1675 - 1682
[7] Preparation and application of air-stable P,N-bidentate ligands for the selective synthesis of δ-lactone via the palladium-catalyzed telomerization of 1,3-butadiene with carbon dioxide
Dai, Yao
Feng, Xiujuan
Wang, Bin
He, Ren
Bao, Ming
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 696 (26) : 4309 - 4314
[8] Inserting CO2 into Terminal Alkynes via Bis-(NHC)-Metal Complexes
Diaz Velazquez, Heriberto
Wu, Zhao-Xuan
Vandichel, Matthias
Verpoort, Francis
[J]. CATALYSIS LETTERS, 2017, 147 (02) : 463 - 471
[9] Palladium-Catalyzed Carboxylative Coupling of Benzyl Chlorides with Allyltributylstannane: Remarkable Effect of Palladium Nanoparticles
Feng, Xiujuan
Sun, Anle
Zhang, Sheng
Yu, Xiaoqiang
Bao, Ming
[J]. ORGANIC LETTERS, 2013, 15 (01) : 108 - 111
[10] Synthesis of Propiolic Acids via Copper-Catalyzed Insertion of Carbon Dioxide into the C-H Bond of Terminal Alkynes
Goossen, Lukas J.
Rodriguez, Nuria
Manjolinho, Filipe
Lange, Paul P.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (17) : 2913 - 2917

← 1 2 3 4 →