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Advisor(s)
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 (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
Description
Keywords
Buchwald–Hartwig coupling Palladium Amination Diarylamines Benzo[b]thiophenes
Citation
Tetrahedron. ISSN 0040-4020. 59:7 (2003) p. 975-981
Publisher
Elsevier