Synthesis of diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups by Buchwald-Hartwig C-N coupling

被引:34
作者
Ferreira, ICFR
Queiroz, MJRP
Kirsch, G
机构
[1] Univ Minho, Dept Quim, P-4710057 Braga, Portugal
[2] Univ Metz, Fac Sci, Lab Ingn Mol & Biochim Pharmacol, F-57045 Metz, France
关键词
Buchwald-Hartwig coupling; palladium; amination; diarylamines; benzo[b]thiophenes; PALLADIUM-CATALYZED AMINATION; NITROGEN BOND FORMATION; ARYL HALIDES; FUNCTIONALIZED OLIGOANILINES; UNSYMMETRICAL TRIARYLAMINES; COMPLEXES; CHEMISTRY; ARYLATION; BROMIDES;
D O I
10.1016/S0040-4020(02)01656-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups, were prepared by Buchwald-Hartwig C-N coupling in moderate to high yields. The conditions used were Pd(OAc)(2) (3 mol%), BINAP as ligand (4 mol%) and Cs2Co3 as base (1.4 equiv.), in toluene at 100degreesC, being 6-bromo or amino benzo[b]thiophenes coupled, respectively, with substituted anilines or phenylbromides. The 6-aminobenzo[b]thiophene derivatives were also prepared by palladium catalyzed C-N coupling of the corresponding 6-bromo compounds with benzophenone imine, followed by acidic hydrolysis of the imino derivatives. When 4-nitrobromobenzene and 4-bromobenzonitrile were used as coupling components, triarylamines were also isolated in small amounts. The presence of a fluorine atom on the phenylbromide highly increases the diarylamine yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:975 / 981
页数:7
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