Selective Monoarylation of Primary Amines Using the Pd-PEPPSI-IPent(Cl) Precatalyst

Selective Monoarylation of Primary Amines Using the Pd-PEPPSI-IPent(Cl) Precatalyst

A single set of reaction conditions for the palladium-catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd-PEPPSI-IPent(Cl) catalyst (PEPPSI=pyridine enhanced precatalyst preparation, sta...

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Veröffentlicht in:Angewandte Chemie International Edition 2015-08, Vol.54 (33), p.9507-9511
Hauptverfasser: Sharif, Sepideh, Rucker, Richard P, Chandrasoma, Nalin, Mitchell, David, Rodriguez, Michael J, Froese, Robert D J, Organ, Michael G
Format: Artikel
Sprache:eng
Schlagworte:
Amination
Amines - chemistry
Butylated Hydroxytoluene - analogs & derivatives
Butylated Hydroxytoluene - chemistry
Catalysis
Halogens - chemistry
Hydrocarbons, Aromatic - chemistry
Palladium - chemistry
Pyridines - chemistry
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Beschreibung
Zusammenfassung:A single set of reaction conditions for the palladium-catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd-PEPPSI-IPent(Cl) catalyst (PEPPSI=pyridine enhanced precatalyst preparation, stabilization, and initiation) with the soluble and nonaggressive sodium salt of BHT (BHT=2,6-di-tert-butyl-hydroxytoluene), both six- and five-membered (hetero)aryl halides undergo efficient and selective amination.
ISSN:1521-3773
DOI:10.1002/anie.201502822