Methoxycarbonylation of styrene to methyl arylpropanoates catalyzed by palladium(II) precursors with 1,1′-bis(diphenylphosphino)metallocenes

被引：38

作者：

Bianchini, C

Meli, A

Oberhauser, W

Parisel, S

Gusev, OV

Kal'sin, AM

Vologdin, NV

Dolgushin, FM

机构：

[1] CNR, ICCOM, Ist Chim Composti Organomet, Area Ric, I-50019 Sesto Fiorentino, Firenze, Italy

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2004年 / 224卷 / 1-2期

基金：

俄罗斯基础研究基金会;

关键词：

1,1 '-bis(diphenylphosphino)metallocenes alkoxycarbonylation; palladium; alkyl arylpropanoates; regioselectivity;

D O I：

10.1016/j.molcata.2004.06.029

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Palladium(II) complexes with 1,1'-bis(diphenylphosphino)ferrocene (dppf), 1,1'-bis(diphenylphosphino)octamethylferrocene (dppomf), 1, 1'-bis(diphenylphosphino)ruthenocene (dppr) and 1, 1'-bis(diphenylphosphino)osmocene (dppo) have been synthesized and used to catalyze the methoxycarbonylation of styrene. Irrespective of the precursor, all the reactions gave methyl phenylpropanoates with prevalence of the linear isomer methyl 3-phenylpropanoate (up to 85% regioselectivity). The highest turnover frequency was obtained with the dppr precursor in the presence of p-toluene sulphonic acid co-catalyst (334 mol of styrene converted (mol of catalyst h)(-1)). A reaction mechanism accounting for both activity and selectivity has been proposed on the basis of operando high-pressure NMR experiments and reactions with model compounds. (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：35 / 49

页数：15

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[41] DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES [J].