An efficient synthesis of carboranyl tetrazoles via alkylation of 5-R-1H-tetrazoles with allylcarboranes

An efficient triflic acid catalyzed regioselective alkylation of 5-R-1H-tetrazoles with readily available allylcarboranes is reported. The suggested synthetic procedure allows the formation of a variety of carboranyl-substituted tetrazoles in a good yield under mild conditions. Transformations of newly synthesized carboranyl tetrazoles under UV irradiation were studied. Allylcarboranes as starting materials were prepared via Pd-catalyzed cross-coupling reaction of iodocarboranes with allylmagnesium bromide.

Graphical abstractThe regioselective synthesis of new o- and m-carborane tetrazoles was developed via the alkylation of 5-R-1H-tetrazoles with available allylcarboranes.Figure optionsDownload full-size imageDownload as PowerPoint slide