Julia-Kocienski-Like Connective C−C and C=C Bond-Forming Reaction

0587192 - ÚEB 2025 RIV DE eng J - Journal Article
Bon, D.J.Y.D. - Chrenko, D. - Kováč, O. - Ferugová, V. - Lasák, Pavel - Fuksová, Markéta - Zálešák, F. - Pospíšil, Jiří
Julia-Kocienski-Like Connective C−C and C=C Bond-Forming Reaction.
Advanced Synthesis & Catalysis. Roč. 366, č. 3 (2024), s. 480-487. ISSN 1615-4150. E-ISSN 1615-4169
R&D Projects: GA MŠMT(CZ) EF16_019/0000738
Institutional support: RVO:61389030
Keywords : coupling reaction * divergence in synthesis * fatty acid synthesis * olefination method * stereoselectivity
OECD category: Organic chemistry
Impact factor: 5.4, year: 2022
Method of publishing: Open access
https://doi.org/10.1002/adsc.202301054

In this paper, we present a one-pot protocol that enables a straightforward and selective transformation of alkyl benzothiazol-2-yl and phenyltetrazol-2-yl sulfones and acyl chlorides into ketones, E-olefins, Z-olefins, and even pyrroles. The final product of the reaction depends on the proper choice of the reaction workup. Notably, the protocol designed for olefin formation allows a switch between E- and Z-olefin formation by the correct choice of the reaction workup. These developed protocols facilitate the formation of all compounds under mild reaction conditions, as evidenced by the synthesis of (nitro)-fatty acids, and the concept can be extended to other product formations, as demonstrated by the synthesis of pyrroles.
Permanent Link: https://hdl.handle.net/11104/0354458