Arylseleninic acid derivative decomposition towards Se(ii)-based electrophiles: an elegant approach to construct 3-selanyl-imidazopyridines

Benzeneseleninic acid (BSA) derivatives were used as an alternative, but extremely useful, source of Se(ii)-based electrophiles, generated in situ by thermal decomposition, to construct C-Se bonds, accessing 3-selanylimidazopyridines after reaction with 2-substituted imidazopyridines. A total of thirty-four derivatives were synthesized in 50-94% yield, seventeen of which were so far unprecedented. A simple and efficient protocol is described, just delivering H2O and diaryl diselenide as by-products. Diaryl diselenides can be easily recovered during the purification process and converted again to BSA for a new reaction.

Automated summary

Benzeneseleninic acid (BSA) derivatives were used as a convenient source of Se(ii)-based electrophiles for the formation of C-Se bonds via thermal decomposition. The reaction with 2-substituted imidazopyridines resulted in the synthesis of 3-selanylimidazopyridines. A total of thirty-four derivatives were prepared, with seventeen of them being previously unreported. The reaction protocol is simple and efficient, yielding only H2O and diaryl diselenide as by-products, which can be easily recovered and reused.