Pd(II) - dppb and syngas catalyze regioselective hydroesterification of terminal alkynes under neutral conditions

被引:12
作者
El Ali, B [1 ]
Tijani, J [1 ]
El-Ghanam, AM [1 ]
机构
[1] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia
关键词
palladium(II); hydroesterification; carbonylation; alcohols; alkynes; unsaturated esters; syngas;
D O I
10.1016/S0040-4039(01)00152-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium(II) regioselectively catalyzes the hydroesterification of terminal alkynes under syngas forming alpha,beta -unsaturated esters 3 and 4 in excellent chemical yields under neutral conditions. The high selectivity for the linear ester 4 was obtained with a catalytic system that includes Pd(II), 1,4-bis(diphenylphosphino)butane (dppb) and CO/H-2 in CH2Cl2 as solvent. The control of the regioselectivity depends strongly upon the type of ligand, the solvent and the use of the syngas mixture. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2385 / 2387
页数:3
相关论文
共 9 条
[1]  
BOLM C, 1998, TRANSITION METALS FI, P49
[2]  
Colquhoun H.M., 1991, CARBONYLATION
[3]   The bite angle makes the difference: a practical ligand parameter for diphosphine ligands [J].
Dierkes, P ;
van Leeuwen, PWNM .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (10) :1519-1529
[4]   EFFICIENT PALLADIUM CATALYSTS FOR THE CARBONYLATION OF ALKYNES [J].
DRENT, E ;
ARNOLDY, P ;
BUDZELAAR, PHM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 455 (1-2) :247-253
[5]   Regioselective control of the thiocarbonylation of terminal acetylenes with arylthiols catalyzed by Pd(II) and diphosphine ligands [J].
El Ali, B ;
Tijani, J ;
El-Ghanam, A ;
Fettouhi, M .
TETRAHEDRON LETTERS, 2001, 42 (08) :1567-1570
[6]  
ELALI B, 1995, J MOL CATAL A-CHEM, V96, P197
[7]   SYNTHESIS OF UNSATURATED ESTERS, INCLUDING TERT-ALKYL ESTERS, BY THE PALLADIUM-CATALYZED CARBONYLATION OF ALKYNES IN THE PRESENCE OF ALCOHOLS AND 1,4-BIS(DIPHENYLPHOSPHINO)BUTANE [J].
ELALI, B ;
ALPER, H .
JOURNAL OF MOLECULAR CATALYSIS, 1991, 67 (01) :29-33
[8]   A novel palladium complex catalyst for carbonylation of alkynes under mild conditions [J].
Jayasree, S ;
Seayad, A ;
Gupte, SP ;
Chaudhari, RV .
CATALYSIS LETTERS, 1999, 58 (04) :213-216
[9]  
Tsuji J., 1995, PALLADIUM REAGENTS C