Palladium(0)-Catalyzed Arylation of Resin-Bound Imidazol-2-ylzinc Chlorides

Sophie Havez; Mikael Begtrup; Per Vedsø; Kim Andersen; Thomas Ruhland

doi:10.1055/s-2001-13407

PAPER

Palladium(0)-Catalyzed Arylation of Resin-Bound Imidazol-2-ylzinc Chlorides

Sophie Havez^a, Mikael Begtrup*^a, Per Vedsø^a, Kim Andersen^b, Thomas Ruhland^b
^a Department of Medicinal Chemistry, The Royal Danish School of Pharmacy, Universitetsparken 2, 2100 Copenhagen, Denmark
^b Medicinal Chemistry Research, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby, Denmark
Fax: +45 35 30 60 40; e-Mail: begtrup@dfh.dk;

Abstract

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Abstract

1-Hydroxyimidazole loaded on Wang resin under Mitsunobu conditions was selectively deprotonated at C-2 by BuLi. The anion formed was then reacted with electrophiles or transmetallated with zinc chloride to give resin-bound imidazolylzinc chloride which was cross-coupled with aryl and heteroaryl iodides under palladium(0) catalysis. Cleavage using TFA-CH₂Cl₂ (1:1) at room temperature afforded 2-aryl/heteroaryl substituted 1-hydroxyimidazoles.

Keywords

solid-phase synthesis - cross-coupling - palladium - zinc compounds - 1-hydroxyimidazole

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Referenzen

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