Tetrahedron

Highly selective synthesis of 4 (5)-aryl-, 2, 4 (5)-diaryl-, and 4, 5-diaryl-1H-imidazoles via Pd-catalyzed direct C-5 arylation of 1-benzyl-1H-imidazole

F Bellina, S Cauteruccio, A Di Fiore, C Marchetti…

Index: Bellina, Fabio; Cauteruccio, Silvia; Di Fiore, Annarita; Marchetti, Chiara; Rossi, Renzo Tetrahedron, 2008 , vol. 64, # 26 p. 6060 - 6072

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Citation Number: 92

Abstract

Highly selective, practical, and efficient protocols for the preparation of 4 (5)-aryl-1H- imidazoles 2, 2, 4 (5)-diaryl-1H-imidazoles 3, and 4, 5-diaryl-1H-imidazoles 1 are described. A key step of these protocols is the regioselective synthesis of 5-aryl-1-benzyl-1H- imidazoles 9 by Pd-catalyzed direct C-5 arylation of commercially available 1-benzyl-1H- imidazole (8) with aryl halides. The three-step synthesis of compounds 3 from 8 also ...