Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions

被引:217
作者
Bellina, F [1 ]
Cauteruccio, S [1 ]
Rossi, R [1 ]
机构
[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
关键词
C-C coupling; synthetic methods; regioselectivity; palladium; copper;
D O I
10.1002/ejoc.200500957
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first palladium- and copper-mediated C-2 arylations of thiazole, oxazole, N-methylimidazole and N-arylimidazoles, as well as of free (NH)-imidazole, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions are described. Complete selectivity has been achieved under these unprecedented conditions, which allow the use of substrates containing base-sensitive groups, such the NH groups of imidazole, benzimidazole or indole, without their prior protection. No N-arylation products were detected in the arylation of free (NH)-imidazole, -benzimidazole and indole. (c) Wiley-VCH Verlag GmbH & Co.
引用
收藏
页码:1379 / 1382
页数:4
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