Palladium on carbon-bromobenzene mediated esterification and transesterification

被引：15

作者：

Aavula, Sanjeev Kumar ^{[1
]}

Chikkulapalli, Anil ^{[1
]}

Hanumanthappa, N. ^{[1
]}

Jyothi, Indira ^{[1
]}

Kumar, C. H. Vinod ^{[1
]}

Manjunatha, Sulur G. ^{[1
]}

机构：

[1] AstraZeneca India Pvt Ltd, Pharmaceut Dev, Bangalore 560024, Karnataka, India

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 42期

关键词：

Esterification; Palladium; Bromobenzene; Transesterification; N-HETEROCYCLIC CARBENES; CARBOXYLIC-ACIDS; MITSUNOBU REACTIONS; MILD; CATALYSTS; ZEOLITES; REAGENTS;

D O I：

10.1016/j.tetlet.2013.08.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of carboxylic acids were converted into their corresponding esters using the Pd/C catalyzed hydrogenation conditions in the presence of catalytic bromobenzene in alcohols and the method could also be applicable for the transesterification of esters. Good to excellent yields were obtained for different aliphatic or aromatic starting materials. The success of this esterification relies on the in situ generation of hydrobromic acid (HBr) from bromobenzene which provides a mild and acidic reaction environment. The palladium catalyst exhibits a remarkable activity and is reusable for up-to three consecutive cycles. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5690 / 5694

页数：5

共 39 条

[1] FORMATION OF A JOJOBA OIL ANALOG BY ESTERIFICATION OF OLEIC-ACID USING ZEOLITES AS CATALYST [J].

ARACIL, J ;

MARTINEZ, M ;

SANCHEZ, N ;

CORMA, A .

ZEOLITES, 1992, 12 (03) :233-236

[2] Mitsunobu synthesis of symmetrical alkyl and polyfluoroalkyl secondary amines [J].

Bálint, AM ;

Bodor, A ;

Gömöry, A ;

Vékey, K ;

Szabó, D ;

Rábai, J .

JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (11-12) :1524-1530

[3]

Baumhof P, 2001, ANGEW CHEM INT EDIT, V40, P3672, DOI 10.1002/1521-3773(20011001)40:19<3672::AID-ANIE3672>3.0.CO

[4]

2-Y

[5] Fresh and calcined supported 12-tungstosilicicacid: Synthesis, characterization and application to some acid catalyzed reactions [J].

Bhatt, Nikunj ;

Patel, Anjali ;

Selvam, Parasuram ;

Sidhpuria, Kalpesh .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 275 (1-2) :14-24

[6] MODIFIED FAUJASITE ZEOLITES AS CATALYSTS IN ORGANIC-REACTIONS - ESTERIFICATION OF CARBOXYLIC-ACIDS IN THE PRESENCE OF HY ZEOLITES [J].

CORMA, A ;

GARCIA, H ;

IBORRA, S ;

PRIMO, J .

JOURNAL OF CATALYSIS, 1989, 120 (01) :78-87

[7] Separation-friendly Mitsunobu reactions: A microcosm of recent developments in separation strategies [J].

Dandapani, S ;

Curran, DP .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (13) :3130-3138

[8] Fluorous Mitsunobu reagents and reactions [J].

Dandapani, S ;

Curran, DP .

TETRAHEDRON, 2002, 58 (20) :3855-3864

[9] Recent advances in the Mitsunobu reaction: Modified reagents and the quest for chromatography-free separation [J].

Dembinski, R .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (13) :2763-2772

[10] Synthesis of fluorous azodicarboxylates: towards cleaner Mitsunobu reactions [J].

Dobbs, AP ;

McGregor-Johnson, C .

TETRAHEDRON LETTERS, 2002, 43 (15) :2807-2810

← 1 2 3 4 →