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

被引：111

作者：

Bellina, Fabio ^{[1
]}

Cauteruccio, Silvia ^{[1
]}

Di Fiore, Annarita ^{[1
]}

Marchetti, Chiara ^{[1
]}

Rossi, Renzo ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

来源：

TETRAHEDRON | 2008年 / 64卷 / 26期

关键词：

imidazoles; direct arylation; regioselectivity; C-H bond activation; biologically active compounds;

D O I：

10.1016/j.tet.2008.01.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 involves the Pd-catalyzed and Cu-mediated direct C-2 arylation of imidazoles 9 with aryl halides under base-free and ligandless conditions. On the other hand, the four-step synthesis of imidazoles 1 from 8 also involves the regioselective bromination of compounds 9 and a Suzuki reaction of the resulting 5-aryl-1-benzyl-4-bromo-1H-imidazoles 11 with arylboronic acids 5 under phase-transfer conditions, followed by N-debenzylation. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6060 / 6072

页数：13

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