Phenyl Sulfones: A Route to a Diverse Family of Trisubstituted Cyclohexenes from Three Independent Nucleophilic Additions.

ABSTRACT: A novel process is described for the synthesis of di- and trisubstituted cyclohexenes from an arene. These compounds are prepared from three independent nucleophilic addition reactions to a phenyl sulfone (PhSO₂R; R = Me, Ph, and NC₄H₈) dihapto-coordinated to the tungsten complex {WTp(NO)(PMe₃)}(Tp = trispyrazolylborate). Such a coordination renders the dearomatized aryl ring susceptible to protonation at a carbon ortho to the sulfone group. The resulting arenium species readily reacts with the first nucleophile to form a dihapto-coordinated sulfonylated diene complex. This complex can again be protonated, and the subsequent nucleophilic addition forms a trisubstituted cyclohexene species bearing a sulfonyl group at an allylic position. Loss of t

SUBMITTER: Simpson SR 

PROVIDER: S-EPMC9205081 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature