Nickel-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of 2-aminobenzimidazoles

A complementary set of Ni- and Cu-based catalyst systems for the selective N-arylation of 2-aminobenzimidazoles have been developed. Selective N-arylation of the primary amine (C-NH2) group was achieved by Ni-catalyzed, boronic acid promoted cross-coupling reactions in air, whereas, selective N-aryl...

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Veröffentlicht in:Organic & biomolecular chemistry 2016-01, Vol.14 (38), p.8989-8997
Hauptverfasser: Kumar, K Anil, Kannaboina, Prakash, Rao, D Nageswar, Das, Parthasarathi
Format: Artikel
Sprache:eng
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Zusammenfassung:A complementary set of Ni- and Cu-based catalyst systems for the selective N-arylation of 2-aminobenzimidazoles have been developed. Selective N-arylation of the primary amine (C-NH2) group was achieved by Ni-catalyzed, boronic acid promoted cross-coupling reactions in air, whereas, selective N-arylation of the azole nitrogen was achieved with Cu-catalysis and aryl halides. These protocols are general and give rapid access to an array of both the N-arylated isomers of 2-aminobenzimidazoles.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01307d