An efficient and general synthesis of furan-2-acetic esters by palladium-catalyzed oxidative carbonylation of (Z)-2-en-4-yn-1-ols

被引:76
作者
Gabriele, B [1 ]
Salerno, G
De Pascali, F
Costa, M
Chiusoli, GP
机构
[1] Univ Calabria, Dipartimento Chim, I-87030 Cosenza, Italy
[2] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy
关键词
D O I
10.1021/jo990848+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of (Z)-2-en-4-yn-1-ols have been carbonylated under oxidative conditions to give substituted furan-a-acetic esters in good yields. The cyclization-alkoxycarbonylation process occurs in alcoholic media at 50-70 degrees C and under 100 atm pressure of a 9:1 mixture of carbon monoxide and air in the presence of catalytic amounts of PdI2 in conjunction with KI. The proposed reaction pathway involves the in situ isomerization of the initially formed (E)-2-[(alkoxycarbonyl)methylene]-2,5-dihydrofuran species, which in some cases have been isolated and shown to be the intermediates.
引用
收藏
页码:7693 / 7699
页数:7
相关论文
共 62 条
[11]   The first stereoselective palladium-catalyzed cyclocarbonylation of beta,gamma-substituted allylic alcohols [J].
Brunner, M ;
Alper, H .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7565-7568
[12]  
CAI JC, 1989, CHEM PHARM BULL, V37, P2976
[13]   SYNTHETIC AND MECHANISTIC ASPECTS OF INORGANIC INSERTION REACTIONS - INSERTION OF CARBON-MONOXIDE [J].
CALDERAZZO, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (05) :299-311
[14]   CARBON-MONOXIDE AS A BUILDING BLOCK IN ORGANIC-SYNTHESIS .2. ONE-STEP SYNTHESIS OF ESTERS BY ALKOXYCARBONYLATION OF NATURALLY-OCCURRING ALLYLBENZENES, PROPENYLBENZENES AND MONOTERPENES [J].
CHENAL, T ;
CIPRES, I ;
JENCK, J ;
KALCK, P ;
PERES, Y .
JOURNAL OF MOLECULAR CATALYSIS, 1993, 78 (03) :351-366
[15]   Sequential reaction of carbon dioxide and carbon monoxide with acetylenic amines in the presence of a palladium catalyst [J].
Chiusoli, GP ;
Costa, M ;
Gabriele, B ;
Salerno, G .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 143 (1-3) :297-310
[16]  
Colquhoun H.M., 1991, CARBONYLATION
[17]   STEREOCHEMISTRY OF THERMOLYTIC BASE-CATALYZED DECARBOXYLATION TO FORM CONJUGATED DIENE-ACIDS - SYNTHESIS USING ETHYLIDENEMALONIC ESTER CONDENSATION [J].
CROMBIE, L ;
CROMBIE, WML .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (10) :1267-1274
[18]   Regioselective palladium(II)-catalyzed synthesis of five- or seven-membered ring lactones and five-, six- or seven-membered ring lactams by cyclocarbonylation methodology [J].
ElAli, B ;
Okuro, K ;
Vasapollo, G ;
Alper, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4264-4270
[19]   CYCLOPENTENONE SYNTHESIS BY DIRECTED CYCLIZATION [J].
FINCH, N ;
FITT, JJ ;
HSU, IHC .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (21) :3191-&
[20]  
FINCKE H, 1969, Patent No. 1919381