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Synlett 2006(12): 1965-1967  
DOI: 10.1055/s-2006-948162
LETTER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of 2-Substituted Imidazoles by Palladium-Catalyzed Cross-Coupling with Benzylzinc Reagents

Josefin E. Utas, Berit Olofsson, Björn Åkermark*
Stockholm University, Department of Organic Chemistry, Arrhenius Laboratory, 106 91 Stockholm, Sweden
Fax: +46(8)154908; e-Mail: Bjorn.Akermark@organ.su.se;
Further Information

Publication History

Received 28 March 2006
Publication Date:
24 July 2006 (online)

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Abstract

Substituted benzylzinc reagents have been used in novel cross-coupling reactions with 2-iodo imidazoles to form compounds containing both a phenol and an imidazole moiety. The ­intramolecular hydrogen-bonding properties of these compounds were subsequently studied.

Key words

cross-coupling - palladium - zinc - benzylation - heterocycles

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4

The calculations will be reported separately together with further analyses of the target compounds.

13

This reagent is also commercially available from Aldrich.

16

Compound 9c was not deprotected due to lack of material.