Radical decarboxylative alkylation onto heteroaromatic bases with trivalent iodine compounds

Abstract

Heteroaromatic bases containing nitrogen atoms were easily alkylated with carboxylic acids in the presence of [bis(trifluoroacetoxy)iodo] benzene and [bis(trifluoroacetoxy)iodo]pentafluorobenzene via radical pathways. Similarly, the alkylation onto heteroaromatic bases was carried out with oxalic acid monoalkyl esters, which were prepared from alcohols and oxalyl dichloride, in the presence of the same trivalent iodine compounds. Moreover, this system was applied to the synthesis of C-nucleosides with the carboxylic acids bearing a sugar moiety.