Novel bis[(1,2,3-triazolyl)methyl]carborane derivatives via regiospecific copper-catalyzed 1,3-dipolar cycloaddition

1,2-Bis(azidomethyl)-о-carborane and 1,7-bis(azidomethyl)-m-carborane, prepared from the corresponding carboranylmethyl triflates and sodium azide, were conveniently functionalized by azide–alkyne cycloaddition affording novel bis[(1,2,3-triazolyl)methyl]carborane derivatives. Regiospecificity of this process was achieved by employing copper(II) acetate hydrate. Reaction of bis[(1,2,3-triazolyl)methyl]carborane derivatives with MeI yielded 3-methyl-1,2,3-triazolium carborane salts.

Graphical abstract1,2-Bis(azidomethyl)-о-carborane and 1,7-bis(azidomethyl)-m-carborane, prepared from the corresponding carboranylmethyl triflates and sodium azide, were conveniently functionalized by azide–alkyne cycloaddition affording novel bis[(1,2,3-triazolyl)methyl]carborane derivatives. Regiospecificity of this process was achieved by employing copper(II) acetate hydrate.Figure optionsDownload full-size imageDownload as PowerPoint slide