Issue 15, 2004
From the journal:

Organic & Biomolecular Chemistry

Heck reaction catalyzed by Pd/C, in a triphasic—organic/Aliquat 336/aqueous—solvent system

Alvise Perosa,*a   Pietro Tundo,a   Maurizio Selva,a   Sergei Zinovyeva  and  Alberto Testaa  

* Corresponding authors

a Dipartimento di Scienze Ambientali dell'Università Ca' Foscari, Consorzio Interuniversitario Nazionale “la Chimica per l'Ambiente” (INCA), Dorsoduro 2137 – 30123 Venezia, Italy
E-mail: alvise@unive.it

Abstract

The rate of the Pd/C catalyzed Heck coupling of Ar-I with CH2[double bond, length as m-dash]CH-R is accelerated tenfold by the presence of Aliquat 336 (A336), a well known phase transfer catalyst, and an ionic liquid. Both when conducted in A336 as solvent, and in an isooctane/A336/aqueous triphasic mixture, the Heck reaction of aryl iodides with electron deficient olefins, catalyzed by Pd/C, proceeds with high yields and selectivity. When KOH is used instead of Et3N, selective formation of the biphenyl rather than the Heck product, is observed. Aryl bromides react more sluggishly, and only the more activated ones undergo the Heck reaction. In the absence of the olefin, aryl halides possessing an electron withdrawing group are reduced to the corresponding Ar-H.

Graphical abstract: Heck reaction catalyzed by Pd/C, in a triphasic—organic/Aliquat 336/aqueous—solvent system

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Article information

DOI
https://doi.org/10.1039/B406822J
Article type
Paper
Submitted
06 May 2004
Accepted
09 Jun 2004
First published
14 Jul 2004

Org. Biomol. Chem., 2004,2, 2249-2252

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Heck reaction catalyzed by Pd/C, in a triphasic—organic/Aliquat 336/aqueous—solvent system

A. Perosa, P. Tundo, M. Selva, S. Zinovyev and A. Testa, Org. Biomol. Chem., 2004, 2, 2249 DOI: 10.1039/B406822J

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