Di- and triazidation of 3-chlorotetrafluoropyridine

3-Chlorotetrafluoropyridine and pentafluoropyridine readily react with an excess of sodium azide in dimethylsulfoxide at room temperature to give corresponding 2,4,6-triazido-3-chloro-5-fluoropyridine and 2,4,6-triazido-3,5-difluoropyridine in high yields. The reaction of asymmetric 3-chlorotetrafluoropyridine with two equimolar amounts of sodium azide under similar reaction conditions occurs regioselectively to give 2,4-diazido-5-chloro-3,6-difluoropyridine as a sole product. 19F, 13C and 15N NMR spectral characteristics of the triazides suggest that these compounds can be of interest as cross-linking reagents for polymer chemistry and as starting materials for organic synthesis.

Graphical abstract3-Chlorotetrafluoropyridine and pentafluoropyridine readily react with an excess of sodium azide in dimethylsulfoxide at room temperature to give corresponding 2,4,6-triazido-3-chloro-5-fluoropyridine and 2,4,6-triazido-3,5-difluoropyridine in high yields. The reaction of asymmetric 3-chlorotetrafluoropyridine with two equimolar amounts of sodium azide under similar reaction conditions occurs regioselectively to give 2,4-diazido-5-chloro-3,6-difluoropyridine as a sole product. 19F, 13C and 15N NMR spectral characteristics of the triazides suggest that these compounds can be of interest as cross-linking reagents for polymer chemistry and as starting materials for organic synthesis.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Mild and facile triazidation of polyfluoropyridines. ► Regioselective 4,6-diazidation of 3-chlorotetrafluoropyridine. ► 19F, 13C and 15N NMR spectroscopic characteristics of new photoactive cross-linking reagents.