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

Abstract

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.