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

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

Angewandte Chemie (International ed. in English) (2015-06-23)
Sepideh Sharif, Richard P Rucker, Nalin Chandrasoma, David Mitchell, Michael J Rodriguez, Robert D J Froese, Michael G Organ
PMID26097000
ABSTRACT

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.