Organometallic catalysis in aqueous-organic two-phase systems: Rhodium-catalyzed coupling reaction of but-3-enoic acid with allyl derivatives; influence of the reaction media

被引：3

作者：

Bottarelli, Paolo ^{[1
]}

Costa, Mirco ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2008年 / 289卷 / 1-2期

关键词：

organometallic catalysis; aqueous-organic two-phase systems; C-C coupling; rhodium; heptadienoic acids;

D O I：

10.1016/j.molcata.2008.04.015

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：

A simple and efficient procedure is described for the synthesis of 2,6- and 3,6-heptadienoic acids and allyl esters consisting of Rh-catalyzed coupling of but-3-enoic acid and allyl derivatives such as allyl bromide, allyl acetate, and allyl methyl carbonate in alkaline water or in alkaline water/organic two-phase systems. 2,6-Heptadienoate derivatives are the main products in water as acids and in biphasic systems as acids and allyl esters. The latter can be selectively obtained via one-pot cascade esterification reaction using allyl bromide in biphasic systems. The nature of organic solvent, the base concentration and the addition of triphenylphosphine (TPP) in biphasic media allow to tune the regioselectivity of the reaction towards 3,6- or 2,6-derivatives. Substituted but-3-enoic acids and ally] bromides, and pent-4-enoic acid led to moderate or poor results. (C) 2008 Elsevier B.V. All rights reserved.

引用

页码：82 / 90

页数：9

共 11 条

[1]

BERSELLINI U, 1979, FUND RES HOMOGENEOUS, P893

[2] Catalysis in water: Highly efficient synthesis of heptadienoic acids by rearrangement of allyl but-3-enoate promoted by Rh(I) complexes [J].

Bottarelli, Paolo ;

Costa, Mirco ;

Gabriele, Bartolo ;

Salerno, Giuseppe ;

Yebeutchou, Roger A. .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 274 (1-2) :87-94

[3] Novel amphiphilic diphosphines: Synthesis, rhodium complexes, use in hydroformylation and rhodium recycling [J].

Buhling, A ;

Elgersma, JW ;

Nkrumah, S ;

Kamer, PCJ ;

vanLeeuwen, PWNM .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (10) :2143-2154

[4] TRANSITION METAL-CATALYZED REARRANGEMENT OF ALLYL BUT-3-ENOATE TO HEPTA-2,6-DIENOIC OR HEPTA-3,6-DIENOIC ACIDS [J].

CHIUSOLI, GP ;

SALERNO, G ;

DALLATOMASINA, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (21) :793-794

[5]

CHIUSOLI GP, 1982, J ORGANOMET CHEM, V238, pC85, DOI 10.1016/S0022-328X(00)83811-5

[6]

CHIUSOLI GP, 1972, ORGANOMET CHEM SYNTH, V1, P439

[7]

Cornils B., 2004, Aqueous-Phase Organometallic Catalysis: Concepts and Applications

[8]

DARENSBOURG DJ, 2004, AQUEOUS PHASE ORGANO, P71

[9] The migrastatin family: Discovery of potent cell migration inhibitors by chemical synthesis [J].

Gaul, C ;

Njardarson, JT ;

Shan, D ;

Dorn, DC ;

Wu, KD ;

Tong, WP ;

Huang, XY ;

Moore, MAS ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (36) :11326-11337

[10]

HERMANN WA, 2004, AQUEOUS PHASE ORGANO, P44

← 1 2 →