From boom to bloom: synthesis of diazidodifluoromethane, its stability and applicability in the ‘click’ reaction

Mykyta Ziabko; Sergeii Suikov; Josef Filgas; Petr Slavíček; Michaela Gazdurová; Lucie Bednárová; Robert Matyáš; Blanka Klepetářová; Tomáš David; Petr Beier

doi:10.1039/D4CC05128A

From boom to bloom: synthesis of diazidodifluoromethane, its stability and applicability in the ‘click’ reaction†

Mykyta Ziabko,

^ab Sergeii Suikov,

^a Josef Filgas,

^c Petr Slavíček,

^c Michaela Gazdurová,^a Lucie Bednárová,

^a Robert Matyáš,^d Blanka Klepetářová,

^a Tomáš David

^a and Petr Beier

*^a

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 160 00 Prague, Czechia
E-mail: beier@uochb.cas.cz

^b Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 166 28 Prague, Czechia

^c Department of Physical Chemistry, University of Chemistry and Technology, Technická 5, 166 28 Prague, Czechia

^d Institute of Energetic Materials, Faculty of Chemical Technology, University of Pardubice, Doubravice 41, 532 10 Pardubice, Czechia

Abstract

Diazidodifluoromethane was prepared from dibromodifluoromethane, sodium azide and an alkanethiolate initiator. It represents the first example of a diazidomethane that is stable enough to be used in synthesis. The stability of (poly)azidomethanes was explored with ab initio calculations. Copper(I)-catalysed azide–alkyne cycloaddition of the title azide with alkynes afforded difluoromethylene-containing bis(1,2,3-triazoles)amenable to Rh(II)-catalysed transannulation with nitriles to difluoromethylene bis(imidazoles).

Chemical Communications

From boom to bloom: synthesis of diazidodifluoromethane, its stability and applicability in the ‘click’ reaction†

Abstract

Supplementary files

Article information

Download Citation

Permissions

From boom to bloom: synthesis of diazidodifluoromethane, its stability and applicability in the ‘click’ reaction

Social activity

Search articles by author

Spotlight

Advertisements