Hydrocarboxylation of Allenes with CO2 Catalyzed by Silyl Pincer-Type Palladium Complex

被引:313
作者
Takaya, Jun [1 ]
Iwasawa, Nobuharu [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan
关键词
D O I
10.1021/ja806677w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tridentate PSiP pincer-type palladium complex-catalyzed hydrocarboxylation of allenes under carbon dioxide to give synthetically useful beta,gamma-unsaturated carboxylic acids was developed. This novel CO2-fixation reaction is thought to proceed through the catalytic generation of sigma-allyl palladium species via hydropalladation of allenes, followed by its regioselective nucleophilic addition to CO, in the presence of an appropriate reducing agent. The reaction is successfully applied to various allenes bearing functional groups such as ester, carbamate, ketone, and alkene, showing high synthetic utility of this protocol.
引用
收藏
页码:15254 / +
页数:3
相关论文
共 31 条
[1]  
Aresta M, 1985, C1 MOL CHEM, V1, P283
[2]   Silicon based phosphines with P-Si-P, P-C-Si-C-P and P-O-Si-O-P linkages and their coordination chemistry and catalytic applications [J].
Balakrishna, MS ;
Chandrasekaran, P ;
George, PP .
COORDINATION CHEMISTRY REVIEWS, 2003, 241 (1-2) :87-117
[3]   Catalytic C-C coupling via transfer hydrogenation: Reverse prenylation, crotylation, and allylation from the alcohol or aldehyde oxidation level [J].
Bower, John F. ;
Skucas, Eduardas ;
Patman, Ryan L. ;
Krische, Michael J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15134-+
[4]   REACTIONS OF CARBON-DIOXIDE WITH CARBON CARBON BOND FORMATION CATALYZED BY TRANSITION-METAL COMPLEXES [J].
BRAUNSTEIN, P ;
MATT, D ;
NOBEL, D .
CHEMICAL REVIEWS, 1988, 88 (05) :747-764
[5]   Phosphinoalkylsilyl complexes.: 12.: Stereochemistry of the tridentate bis(diphenylphosphinopropyl)silyl (biPSi) framework:: Complexation that introduces "face discrimination" at coordinatively unsaturated metal centers.: X-ray crystal and molecular structures of Pt[SiMe(CH2CH2CH2PPh2)2]Cl, IrH[SiMe(CH2CH2CH2PPh2)2]Cl, and RuH[SiMe(CH2CH2CH2PPh2)2](CO)2 [J].
Brost, RD ;
Bruce, GC ;
Joslin, FL ;
Stobart, SR .
ORGANOMETALLICS, 1997, 16 (26) :5669-5680
[6]  
DERIEN S, 1990, SYNLETT, P361
[7]   THE PALLADIUM CATALYZED REACTION OF CARBON-DIOXIDE WITH ALLENE [J].
DOHRING, A ;
JOLLY, PW .
TETRAHEDRON LETTERS, 1980, 21 (32) :3021-3024
[8]   DIRECT SYNTHESIS OF ALKYL 2-ALKYNOATES FROM ALK-1-YNES, CO2, AND BROMOALKANES CATALYZED BY COPPER(I) OR SILVER(I) SALT [J].
FUKUE, Y ;
OI, S ;
INOUE, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2091-2091
[9]   (Phosphinoalkyl)silanes .3. Poly(o-(diphenylphosphino)benzyl)silanes: Synthesis, spectroscopic properties, and complexation at platinum or iridium [J].
Gossage, RA ;
McLennan, GD ;
Stobart, SR .
INORGANIC CHEMISTRY, 1996, 35 (06) :1729-&
[10]  
Johansson R, 2007, DALTON T, P488, DOI 10.1039/b614037h