Pd-catalyzed decarboxylative cross-coupling of 2-carboxyazine N-oxides with various (hetero)aryl halides

Abstract

Decarboxylative cross-coupling reactions of substituted 2-carboxyazine N-oxides, with a variety of (hetero)aryl halides, by bimetallic Pd(0)/Cu(I) and Pd(0)/Ag(I) catalysis are reported. Two possible pathways, a conventional bimetallic-catalyzed decarboxylative arylation, as well as a protodecarboxylative/direct C-H arylation sequence have been considered. These methods provide the first general decarboxylative arylation methodology for the 2-carboxyazine series.

Keywords: 2-carboxyazine N-oxides; catalysis; cross-coupling; palladium.