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Title: Synthesis of diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups by Buchwald–Hartwig C–N coupling
Authors: Ferreira, Isabel C.F.R.
Queiroz, Maria João R.P.
Kirsch, Gilbert
Keywords: Buchwald–Hartwig coupling
Issue Date: 2003
Publisher: Elsevier
Citation: Tetrahedron. ISSN 0040-4020. 59:7 (2003) p. 975-981
Abstract: 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 1008C, 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
ISSN: 0040-4020
Appears in Collections:BB - Artigos em Revistas Indexados ao ISI/Scopus

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