Novel rhodium catalyst for asymmetric hydroformylation of styrene: Study of electronic and steric effects of phosphorus seven-membered ring ligands

被引：28

作者：

Erre, Giulia ^{[1
]}

Enthaler, Stephan ^{[1
]}

Junge, Kathrin ^{[1
]}

Gladiali, Serafino ^{[2
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany

[2] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2008年 / 280卷 / 1-2期

关键词：

asymmetric hydroformylation; rhodium; monodentate phosphines;

D O I：

10.1016/j.molcata.2007.10.023

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：

The asymmetric hydroformylation of styrene catalysed by rhodium complexes modified by monodentate phosphepine ligands has been investigated. The effects of a systematic variation of the phosphorus substituent on catalytic activity and selectivity are reported as well as the outcome of a combinatorial approach for the formation of mixed ligands complexes with several commercially available ligands. Effective catalytic systems have been devised for the reaction that provide for full conversion within 24h and regioselectivity up to 96% in the branched aldehyde and enantioselectivities up to 48%. The use of bidentate ligands built up by binaphthyl-supported seven-membered phosphacyclic units does not allow for further improvement in the reaction outcome. (C) 2007 Elsevier B.V. All rights reserved.

引用

页码：148 / 155

页数：8

共 55 条

[1] ASYMMETRIC HYDROFORMYLATION [J].

AGBOSSOU, F ;

CARPENTIER, JF ;

MORTREAUX, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2485-2506

[2] THE CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS .15. P-31 NUCLEAR MAGNETIC-RESONANCE STUDIES OF THE DONOR PROPERTIES OF HETEROARYLPHOSPHINES TOWARDS SELENIUM AND PLATINUM(II) [J].

ALLEN, DW ;

TAYLOR, BF .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1982, (01) :51-54

[3] Evaluation of asymmetric hydrogenation ligands in asymmetric hydroformylation reactions. Highly enantioselective ligands based on bis-phosphacycles [J].

Axtell, Alex T. ;

Klosin, Jerzy ;

Abboud, Khalil A. .

ORGANOMETALLICS, 2006, 25 (21) :5003-5009

[4] Highly regio- and enantioselective asymmetric hydroformylation of olefins mediated by 2,5-disubstituted phospholane ligands [J].

Axtell, AT ;

Cobley, CJ ;

Klosin, J ;

Whiteker, GT ;

Zanotti-Gerosa, A ;

Abboud, KA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (36) :5834-5838

[5]

Babin J. E., 1993, World Patent, Patent No. [WO 9303839, 9303839]

[6] CHIRAL ARYL DIPHOSPHITES - A NEW CLASS OF LIGANDS FOR HYDROCYANATION CATALYSIS [J].

BAKER, MJ ;

PRINGLE, PG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1292-1293

[7]

Beller M., 2004, TRANSITION METALS OR, V1, P29

[8] THE ASYMMETRIC HYDROFORMYLATION IN THE SYNTHESIS OF PHARMACEUTICALS [J].

BOTTEGHI, C ;

PAGANELLI, S ;

SCHIONATO, A ;

MARCHETTI, M .

CHIRALITY, 1991, 3 (04) :355-369

[9]

Breeden S, 2000, ANGEW CHEM INT EDIT, V39, P4106, DOI 10.1002/1521-3773(20001117)39:22<4106::AID-ANIE4106>3.0.CO

[10]

2-L

← 1 2 3 4 5 6 →