PALLADIUM-CATALYZED HYDROXYCARBONYLATION OF VINYL AND ARYL TRIFLATES - SYNTHESIS OF ALPHA,BETA-UNSATURATED AND AROMATIC CARBOXYLIC-ACIDS

被引:57
作者
CACCHI, S [1 ]
LUPI, A [1 ]
机构
[1] UNIV CATTOLICA SACRO CUORE, FAC MED & CHIRURG A GEMELLI,IST CHIM,CNR, CTR STUDIO, I-00168 ROME, ITALY
关键词
D O I
10.1016/S0040-4039(00)74824-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed hydroxycarbonylation of vinyl and aryl triflates, under a CO balloon, in the presence of potassium acetate affords alpha,beta-unsaturated and aromatic carboxylic acids with one more carbon in good to high yield. The nature of the solvent and of the ligand have been proved to be crucial for the success of the reaction. Vinyl triflates undergo the hydroxycarbonylation at room temperature in DMF in the presence of Pd(OAc)2(PPh3)2. Aryl triflates produce best results at 60-degrees-C in DMSO in the presence of Pd(OAC)2 and 1,1-bis (diphenylphosphino)ferrocene (dppf).
引用
收藏
页码:3939 / 3942
页数:4
相关论文
共 19 条
[1]   DIMETHYL SULFOXIDE-ACID ANHYDRIDE MIXTURES FOR OXIDATION OF ALCOHOLS [J].
ALBRIGHT, JD ;
GOLDMAN, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (10) :2416-&
[2]   BETA-ARYL AND BETA-VINYL-ALPHA,BETA-DIDEHYDRO-ALPHA-AMINOACID DERIVATIVES THROUGH THE PALLADIUM-CATALYZED REACTION OF ARYL AND VINYL TRIFLATES WITH METHYL ALPHA-ACETAMIDOACRYLATE [J].
ARCADI, A ;
CACCHI, S ;
MARINELLI, F ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON, 1990, 46 (20) :7151-7164
[3]   PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES AND VINYL ARYL HALIDES WITH 4-ALKYNOIC ACIDS - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-DELTA-VINYL ARYL-GAMMA-METHYLENE-GAMMA-BUTYROLACTONES [J].
ARCADI, A ;
BURINI, A ;
CACCHI, S ;
DELMASTRO, M ;
MARINELLI, F ;
PIETRONI, BR .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :976-982
[4]   AN INVESTIGATION OF THE PALLADIUM-CATALYZED, FORMATE-MEDIATED HYDROXYCARBONYLATION OF OPTICALLY-ACTIVE 1-ARYLETHYL ESTERS [J].
BAIRD, JM ;
KERN, JR ;
LEE, GR ;
MORGANS, DJ ;
SPARACINO, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1928-1933
[5]   TRANS-(DIMETHYL SULFOXIDE-O)(DIMETHYL SULFOXIDE-S)BIS(TRIFLUOROACETATO)PALLADIUM(II) - ALTERNATIVE LIGATION MODES OF AN AMBIDENTATE LIGAND [J].
BANCROFT, DP ;
COTTON, FA ;
VERBRUGGEN, M .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :1289-1292
[6]  
CACCHI S, 1990, ORG SYNTH, V68, P138
[7]   PALLADIUM-CATALYZED REDUCTION OF ENOL TRIFLATES TO ALKENES [J].
CACCHI, S ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1984, 25 (42) :4821-4824
[8]   PALLADIUM-CATALYZED CARBONYLATION OF ARYL TRIFLATES - SYNTHESIS OF ARENECARBOXYLIC ACID-DERIVATIVES FROM PHENOLS [J].
CACCHI, S ;
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1986, 27 (33) :3931-3934
[9]   PALLADIUM-CATALYZED CARBONYLATION OF ENOL TRIFLATES - A NOVEL METHOD FOR ONE-CARBON HOMOLOGATION OF KETONES TO ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES [J].
CACCHI, S ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1985, 26 (08) :1109-1112
[10]   A NOVEL-APPROACH TO ALPHA-KETO ACID-DERIVATIVES VIA PALLADIUM-CATALYZED ARYLATION AND VINYLATION OF METHYL ALPHA-METHOXYACRYLATE [J].
CACCHI, S ;
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1987, 28 (26) :3039-3042