Ruthenium Catalyzed Mechanochemical Transformation of Sulfonamide Group to Fluoro, Trifluoromethyl, and Trifluoromethoxy Functionalities
A convenient route for the mechanochemical synthesis of fluorinated aromatic compounds, that is, fluoro, trifluoromethyl, and trifluoromethoxy arenes, has been developed via pyrylium tetrafluoroborate (Pyry-BF<sub>4</sub>)-mediated desulfonamidative cross-coupling of primary sulfonamides under the synergy of a piezoelectric material BaTiO<sub>3</sub>, and Ru-catalysis. This is the first-ever report on the selective transformation of sulfonamide (SO<sub>2</sub>NH<sub>2</sub>) functionality to CF<sub>3</sub>/OCF<sub>3</sub>/F group in a single step under mechanochemical ball-milling conditions. Considering the importance of primary sulfonamides as the valuable pharmacophores, the present desulfonamidative cross-coupling approach could have potential to get synthetic utility in pharmaceutical industries for the late-stage functionalization of sulfonamide drugs and related active pharmaceutical ingredients (APIs).
Authors
- Sehrish Sarfaraz (ORCID: https://orcid.org/0000-0002-1286-9331)
- Ronak V. Prajapati (ORCID: https://orcid.org/0000-0002-6945-6925)
- Viktor O. Iaroshenko (ORCID: https://orcid.org/0000-0002-5647-5326)
- Khurshid Ayub (ORCID: https://orcid.org/0000-0003-0990-1860)
- Oleksandr Shalimov (ORCID: https://orcid.org/0000-0002-1538-3206)
- Vaibhav D. Prajapati (ORCID: https://orcid.org/0000-0002-0389-5925)
- Satenik Mkrtchyan (ORCID: https://orcid.org/0000-0001-7081-9802)
- Vishal B. Purohit (ORCID: https://orcid.org/0000-0002-9392-8136)
Institutions
- National Academy of Sciences of Ukraine (UA)
- Gulf University for Science & Technology (KW)
- Abbottabad University of Science and Technology (PK)
- Charotar University of Science and Technology (IN)
- Institute of Organic Chemistry (UA)
- Georgian American University (GE)
- Sardar Patel University (IN)
- Matej Bel University (SK)
- Chitkara University (IN)
Publication Details
- Journal
- Chemistry - An Asian Journal
- Published
- 2025-04-09
- DOI
- https://doi.org/10.1002/asia.202500221
- Citations
- 2
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.58
Funders
- Agentúra na Podporu Výskumu a Vývoja