Selective, efficient and functional group-tolerant CuOAc-mediated N-arylation of 1H-indoles and 9H-carbazole with aryl iodides under base-free and ligandless conditions

被引:47
作者
Bellina, Fabio [1 ]
Calandri, Chiara [1 ]
Cauteruccio, Silvia [1 ]
Rossi, Renzo [1 ]
机构
[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
关键词
C-N coupling; copper; selectivity; synthetic methods; indoles; carbazole;
D O I
10.1002/ejoc.200601084
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
CuOAc-Mediated N-arylation of 1H-indole derivatives and 1H-carbazole with aryl iodides under base-free and ligandless conditions provides the required N-arylazoles with complete N-selectivity and in moderate to good yields. The experimental conditions for this new version of the Ullmann reaction allow an unprecedented tolerance of functional groups and facilitate the workup of the reaction mixtures and isolation of the required chemically pure reaction products. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
引用
收藏
页码:2147 / 2151
页数:5
相关论文
共 50 条
[1]   Serotonin 5-HT2 receptor, dopamine D-2 receptor, and alpha(1) adrenoceptor antagonists. Conformationally flexible analogues of the atypical antipsychotic sertindole [J].
Andersen, K ;
Liljefors, T ;
Hyttel, J ;
Perregaard, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) :3723-3738
[2]   The copper-catalyzed N-arylation of indoles [J].
Antilla, JC ;
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688
[3]   Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Rossi, R .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) :1379-1382
[4]   Regiocontrolled synthesis of 1,2-diaryl-1H-imidazoles by palladium- and copper-mediated direct coupling of 1-aryl-1H-imidazoles with aryl halides under ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Mannina, L ;
Rossi, R ;
Viel, S .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (03) :693-703
[5]   Regioselective synthesis of 1,5-diaryl-1H-imidazoles by palladium-catalyzed direct arylation of 1-aryl-1H-imidazoles [J].
Bellina, F ;
Cauteruccio, S ;
Mannina, L ;
Rossi, R ;
Viel, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3997-4005
[6]  
BELLINA F, 2006, 22 EUR C HET CHEM BA
[7]   Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides [J].
Bellina, Fabio ;
Calandri, Chiara ;
Cauteruccio, Silvia ;
Rossi, Renzo .
TETRAHEDRON, 2007, 63 (09) :1970-1980
[8]   Synthesis of N-aryl indole-2-carboxylates via an intramolecular palladium-catalysed annulation of didehydrophenylalanine derivatives [J].
Brown, JA .
TETRAHEDRON LETTERS, 2000, 41 (10) :1623-1626
[9]   Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions [J].
Cai, Q ;
Zhu, W ;
Zhang, H ;
Zhang, YD ;
Ma, DW .
SYNTHESIS-STUTTGART, 2005, (03) :496-499
[10]   Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].
Cristau, HJ ;
Cellier, PP ;
Spindler, JF ;
Taillefer, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622