Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/2254

TitleSynthesis of diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups by Buchwald-Hartwig C-N coupling
Author(s)Ferreira, Isabel C. F. R.
Queiroz, Maria João R. P.
Kirsch, G.
KeywordsBuchwald-Hartwig coupling
Palladium
Amination
Diarylamines
Benzo[b]thiophenes
Issue date2003
PublisherElsevier
JournalTetrahedron
Citation"Tetrahedron". 59 (2003) 975-981.
Abstract(s)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 (3mol %), BINAP as ligand (4mol %) and Cs2CO3 as base (1.4 equiv.), in toluene at 100 oC, 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.
TypeArticle
URIhttp://hdl.handle.net/1822/2254
DOI10.1016/S0040-4020(02)01656-3
ISSN0040-4020
Peer-Reviewedyes
AccessOpen access
Appears in Collections:CDQuim - Artigos (Papers)

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