Oxidative addition of aryl and benzyl trifluoroacetates to zerovalent palladium complexes with two modes of C-O bond cleavage processes

被引：41

作者：

Nagayama, K ^{[1
]}

Shimizu, I ^{[1
]}

Yamamoto, A ^{[1
]}

机构：

[1] Waseda Univ, Grad Sch Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1999年 / 72卷 / 04期

关键词：

D O I：

10.1246/bcsj.72.799

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The aryl trifluoroacetates oxidatively added to a zerovalent palladium complex 2a with acyl-O bond cleavage under mild conditions to give the corresponding trans-(aryloxo)(trifluoroacetyl)palladium complexes 3a-3c. But 4-nitrophenyl trifluoroacetate reacted with 2a to yield cis-[Pd(OC6H4-4-NO2)(2) (PMe3)(2)] 3d, which was produced with C-O bond activation followed by disproportionation reaction. In contrast, benzyl trifluoroacetates reacted with the Pd(0) complex with benzyl-O bond fission to form benzyl(trifluoroacetato)palladium complexes 4a-4d. Complexes 4a-4d are in equilibrium in solutions between trans and cis isomers, with the proportion of the cis isomer increasing in polar solvents. Palladium-catalyzed carbonylation of benzyl trifluoroacetate has been achieved in the presence of benzyl alcohol and triethylamine to yield benzyl phenylacetate.

引用

页码：799 / 803

页数：5

共 32 条

[1]

[Anonymous], ADV ORGANOMET CHEM

[2] 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

[3]

BERENBLYUM AS, 1976, KOORDINATS KHIM, V2, P845

[4] MONOMERIC METAL-HYDROXIDES, ALKOXIDES, AND AMIDES OF THE LATE TRANSITION-METALS - SYNTHESIS, REACTIONS, AND THERMOCHEMISTRY [J].

BRYNDZA, HE ;

TAM, W .

CHEMICAL REVIEWS, 1988, 88 (07) :1163-1188

[5]

Collman J.P., 1987, PRINCIPLES APPL ORGA

[6]

Crabtree R.H., 1994, ORGANOMETALLIC CHEM

[7] NOVEL CATALYTIC CHEMISTRY OF IRIDIUM POLYHYDRIDE COMPLEXES [J].

GOLDMAN, AS ;

HALPERN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (24) :7537-7539

[8] CARBON OXYGEN BOND-CLEAVAGE OF ESTERS PROMOTED BY HYDRIDO AND ALKYLCOBALT(I) COMPLEXES HAVING TRIPHENYLPHOSPHINE LIGANDS - ISOLATION OF AN INSERTION INTERMEDIATE AND MOLECULAR-STRUCTURE OF PHENOXOTRIS(TRIPHENYLPHOSPHINE)COBALT(I) [J].

HAYASHI, Y ;

YAMAMOTO, T ;

YAMAMOTO, A ;

KOMIYA, S ;

KUSHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) :385-391

[9] SELECTIVE CLEAVAGE OF C-O BONDS IN ESTERS THROUGH OXIDATIVE ADDITION TO NICKEL(0) COMPLEXES [J].

ISHIZU, J ;

YAMAMOTO, T ;

YAMAMOTO, A .

CHEMISTRY LETTERS, 1976, (10) :1091-1094

[10] DIALKYLPALLADIUM(II) COMPLEXES - SYNTHESES, CHARACTERIZATIONS, AND REACTIONS WITH CO, I2, AND CH3I [J].

ITO, T ;

TSUCHIYA, H ;

YAMAMOTO, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (05) :1319-1327

← 1 2 3 4 →