Heteroaryl sulfonamide synthesis: scope and limitations

0560393 - ÚEB 2023 RIV GB eng J - Journal Article
Iakovenko, Roman - Chrenko, Daniel - Kristek, J. - Desmedt, E. - Zálešák, F. - De Vleeschouwer, F. - Pospíšil, Jiří
Heteroaryl sulfonamide synthesis: scope and limitations.
Organic & Biomolecular Chemistry. Roč. 20, č. 15 (2022), s. 3154-3159. ISSN 1477-0520. E-ISSN 1477-0539
R&D Projects: GA MŠMT(CZ) EF16_019/0000738
Institutional support: RVO:61389030
Keywords : PRACTICAL SYNTHESIS * SULFONYL * THIOLS
OECD category: Biochemical research methods
Impact factor: 3.2, year: 2022
Method of publishing: Open access
https://doi.org/10.1039/d2ob00345g

Heteroaryl sulfonamides are important structural motifs in the medicinal and agrochemical industries. However, their synthesis often relies on the use of heteroaryl sulfonyl chlorides, which are unstable and toxic reagents. Herein, we report a protocol that allows direct oxidative coupling of heteroaryl thiols and primary amines, readily available and inexpensive commodity chemicals. The transformation proceeds under mild reaction conditions and yields the desired N-alkylated sulfonamides in good yields. N-alkyl heteroaryl sulfonamides can be further transformed using a microwave-promoted Fukuyama-Mitsunobu reaction to N,N-dialkyl heteroaryl sulfonamides. The developed protocols thus enable the preparation of previously difficult to prepare sulfonamides (toxic reagents, harsh conditions, and low yields) under mild conditions.
Permanent Link: https://hdl.handle.net/11104/0333312