Sequential N-Arylation of Primary Amines as a Route To Alkyldiarylamines

The synthesis of unsymmetrical alkyldiarylamines from a primary amine and two aryl bromides is described. A catalyst system composed of Pd(OAc)2/(rac)-BINAP is used to prepare an alkylarylamine (1) from a primary amine and aryl bromide. The palladium-catalyzed arylation of 1, by means of a different...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 64; no. 16; pp. 6019 - 6022
Main Authors Harris, Michele C, Geis, Oliver, Buchwald, Stephen L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.08.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ARYL BROMIDES
LIGANDS
UTILITY
COMPLEXES
PALLADIUM-CATALYZED AMINATION
NITROGEN BOND FORMATION
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Summary:The synthesis of unsymmetrical alkyldiarylamines from a primary amine and two aryl bromides is described. A catalyst system composed of Pd(OAc)2/(rac)-BINAP is used to prepare an alkylarylamine (1) from a primary amine and aryl bromide. The palladium-catalyzed arylation of 1, by means of a different catalyst system, affords an alkyldiarylamine. The efficiency of each catalyst for the second step depends on the electronic nature of the substrates. This method has reasonable generality and compatiblity with base-sensitive functional groups.
Bibliography:istex:6E9D3F5D5C172333D8A7C4F1E5DB90433B2A8FAB
ark:/67375/TPS-DCHRQ5SC-Q
ISSN:0022-3263
1520-6904
DOI:10.1021/jo990568u