Synthesis of Azidodifluoromethyl Phenyl Sulfone and Its Use as a Synthetic Equivalent of the Azidodifluoromethyl Anion

0572194 - ÚOCHB 2024 RIV US eng J - Journal Article
Ziabko, Mykyta - Klepetářová, Blanka - Beier, Petr
Synthesis of Azidodifluoromethyl Phenyl Sulfone and Its Use as a Synthetic Equivalent of the Azidodifluoromethyl Anion.
Journal of Organic Chemistry. Roč. 88, č. 11 (2023), s. 6939-6946. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA ČR(CZ) GA23-04659S
Institutional support: RVO:61388963
Keywords : copper-free * azides
OECD category: Organic chemistry
Impact factor: 3.6, year: 2022
Method of publishing: Open access
https://doi.org/10.1021/acs.joc.3c00256

Azidodifluoromethyl phenyl sulfone, a new stable fluorinated azide, was synthesized on a multi-gram scale from difluoromethyl phenyl sulfone. The synthetic utility of the title azide in the preparation of N-difluoro(phenylsulfonyl)methyl-1,2,3-triazoles was demonstrated on examples of azide–alkyne cycloaddition reactions. Subsequent reductive desulfonylation/silylation afforded N-difluoro(trimethylsilyl)methyl-1,2,3-triazoles, and rhodium(II)-catalyzed transannulation with nitriles provided N-difluoro(phenylsulfonyl)methyl-substituted imidazoles. The title azide thus represents a synthetic equivalent of the azidodifluoromethyl anion.
Permanent Link: https://hdl.handle.net/11104/0342966


Research data: CCDC