From boom to bloom: synthesis of diazidodifluoromethane, its stability and applicability in the ‘click’ reaction
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 <i>ab initio</i> 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).
Authors
- Petr Slavı́ček (ORCID: https://orcid.org/0000-0002-5358-5538)
- Petr Beier (ORCID: https://orcid.org/0000-0002-0888-7465)
- Lucie Bednářová (ORCID: https://orcid.org/0000-0003-3367-0193)
- Josef Filgas (ORCID: https://orcid.org/0000-0003-4840-0671)
- Tomáš David (ORCID: https://orcid.org/0000-0003-1146-9448)
- S. Yu. Suikov (ORCID: https://orcid.org/0000-0002-6556-3221)
- Blanka Klepetářová (ORCID: https://orcid.org/0000-0003-3916-7839)
- Robert Matyáš (ORCID: https://orcid.org/0000-0002-8049-0315)
- Mykyta Ziabko (ORCID: https://orcid.org/0000-0003-4918-152X)
- Michaela Gazdurová
Institutions
- University of Pardubice (CZ)
- Charles University (CZ)
- Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry (CZ)
- University of Chemistry and Technology, Prague (CZ)
Publication Details
- Journal
- Chemical Communications
- Published
- 2024-11-20
- DOI
- https://doi.org/10.1039/d4cc05128a
- Citations
- 3
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.62