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

Author:

Bon David J.‐Y. D.1,Chrenko Daniel2,Kováč Ondřej1,Ferugová Vendula1,Lasák Pavel3,Fuksová Markéta32,Zálešák František1,Pospíšil Jiří132

Affiliation:

1. Department of Organic Chemistry Faculty of Science Palacky University tř. 17. listopadu 1192/12 CZ-771 46 Olomouc Czech Republic

2. Department of Chemical Biology Faculty of Science Palacky University Šlechtitelů 27 783 71 Olomouc Czech Republic

3. Laboratory of Growth Regulators Palacký University & Institute of Experimental Botany AS CR Šlechtitelů 27 783 71 Olomouc Czech Republic Affiliation

Abstract

AbstractIn 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.

Publisher

Wiley

Subject

General Chemistry

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