Azaphosphatranes as Structurally Tunable Organocatalysts for Carbonate Synthesis from CO2 and Epoxides

被引:167
作者
Chatelet, Bastien [1 ]
Joucla, Lionel [1 ]
Dutasta, Jean-Pierre [1 ]
Martinez, Alexandre [1 ]
Szeto, Kai C. [2 ]
Dufaud, Veronique [2 ]
机构
[1] Univ Lyon, Ecole Normale Super Lyon, CNRS, Chim Lab, F-69364 Lyon, France
[2] Univ Lyon 1, Lab Chim Catalyse Polymere Proc C2P2, CNRS, CPE Lyon, F-69616 Villeurbanne, France
关键词
LEWIS-BASE CATALYST; PROPYLENE CARBONATE; ALPHA; BETA-UNSATURATED ESTERS; IONIC LIQUIDS; DIOXIDE; COMPLEX; PROAZAPHOSPHATRANES; P(I-PRNCH2CH2)(3)N; CONVERSION; FLUORIDES;
D O I
10.1021/ja402053d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three azaphosphatranes were used as organocatalysts for the synthesis of cyclic carbonates from CO2 and epoxides. They proved to be efficient single-component, metal-free catalysts for the reaction of simple or activated epoxides (styrene oxide, epichlorohydrin, glycidyl methyl ether) with CO2 under mild reaction conditions, displaying high stability and productivity over several days of reaction. Substitution patterns on the catalyst were shown to affect activity and stability. Kinetic analysis allowed investigation of the reaction mechanism.
引用
收藏
页码:5348 / 5351
页数:4
相关论文
共 46 条
[31]   Aspects of carbon dioxide utilization [J].
Omae, Iwao .
CATALYSIS TODAY, 2006, 115 (1-4) :33-52
[32]  
PUDOVIK MA, 1981, ZH OBSHCH KHIM+, V51, P530
[33]   An Electron-Rich Proazaphosphatrane for Isocyanate Trimerization to Isocyanurates [J].
Raders, Steven M. ;
Verkade, John G. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5308-5311
[34]   Encaging the Verkade's Superbases: Thermodynamic and Kinetic Consequences [J].
Raytchev, Pascal Dimitrov ;
Martinez, Alexandre ;
Gornitzka, Heinz ;
Dutasta, Jean-Pierre .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) :2157-2159
[35]   Transformation of carbon dioxide [J].
Sakakura, Toshiyasu ;
Choi, Jun-Chul ;
Yasuda, Hiroyuki .
CHEMICAL REVIEWS, 2007, 107 (06) :2365-2387
[36]   Organic Carbonates as Solvents in Synthesis and Catalysis [J].
Schaeffner, Benjamin ;
Schaeffner, Friederike ;
Verevkin, Sergey P. ;
Boerner, Armin .
CHEMICAL REVIEWS, 2010, 110 (08) :4554-4581
[37]   Organic carbonates [J].
Shaikh, AAG ;
Sivaram, S .
CHEMICAL REVIEWS, 1996, 96 (03) :951-976
[38]   Global challenges and strategies for control, conversion and utilization of CO2 for sustainable development involving energy, catalysis, adsorption and chemical processing [J].
Song, Chunshan .
CATALYSIS TODAY, 2006, 115 (1-4) :2-32
[39]   P(RNCH2CH2)3N:: Catalysts for the head-to-tail dimerization of methyl acrylate [J].
Su, WP ;
McLeod, D ;
Verkade, JG .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9499-9501
[40]   P(i-BuNCH2CH2)3N:: An efficient promoter for the nucleophilic aromatic substitution reaction of aryl fluorides with aryl TBDMS (or TMS) ethers [J].
Urgaonkar, S ;
Verkade, JG .
ORGANIC LETTERS, 2005, 7 (15) :3319-3322