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
[11]   Organic solvent-free process for the synthesis of propylene carbonate from supercritical carbon dioxide and propylene oxide catalyzed by insoluble ion exchange resins [J].
Du, Y ;
Cai, F ;
Kong, DL ;
He, LN .
GREEN CHEMISTRY, 2005, 7 (07) :518-523
[12]   [HP(HNCH2CH2)3N]NO3:: an efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions [J].
Fetterly, BA ;
Jana, NK ;
Verkade, JG .
TETRAHEDRON, 2006, 62 (2-3) :440-456
[13]  
Halmann M.M., 1993, CHEM FIXATION CARBON
[14]   New procedure for recycling homogeneous catalyst:: propylene carbonate synthesis under supercritical CO2 conditions [J].
He, LN ;
Yasuda, H ;
Sakakura, T .
GREEN CHEMISTRY, 2003, 5 (01) :92-94
[15]   REACTIONS OF AMINOPHOSPHINES WITH CARBON DISULFIDE [J].
JENSEN, KA ;
DAHL, O ;
ENGELSHE.L .
ACTA CHEMICA SCANDINAVICA, 1970, 24 (04) :1179-&
[16]   HOMOGENEOUS HYDROGENATION OF CARBON-DIOXIDE [J].
JESSOP, PG ;
IKARIYA, T ;
NOYORI, R .
CHEMICAL REVIEWS, 1995, 95 (02) :259-272
[17]   A rapid and effective synthesis of propylene carbonate using a supercritical CO2-ionic liquid system [J].
Kawanami, H ;
Sasaki, A ;
Matsui, K ;
Ikushima, Y .
CHEMICAL COMMUNICATIONS, 2003, (07) :896-897
[18]  
Kim HS, 2000, ANGEW CHEM INT EDIT, V39, P4096, DOI 10.1002/1521-3773(20001117)39:22<4096::AID-ANIE4096>3.3.CO
[19]  
2-0
[20]   Synthesis of new proazaphosphatranes and their application in organic synthesis [J].
Kisanga, PB ;
Verkade, JG .
TETRAHEDRON, 2001, 57 (03) :467-475