Assembly of unsymmetrical 1,3,5-triarylbenzenes via tandem reaction of β-arylethenesulfonyl fluorides and α-cyano-β-methylenones

08 February 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A transition-metal-free tandem reaction of β-arylethenesulfonyl fluorides and α-cyano-β-methylenones has been revealed. In the presence of cesium carbonate, 2-arylethenesulfonyl fluorides react with α-cyano-β-methylenones through a tandem Diels-Alder cycloaddition/sulfur (VI) fluoride exchange/elimination process to afford cyclohexadiene, which further undergoes decyanolative aromatization in one-pot to produce 1,3,5-triarylbenzenes in moderate to good yields. In addition, direct oxidative aromatization of cyclohexadiene intermediate will construct 2,4,6-triarylbenzonitriles.

Keywords

tandem reaction
sulfur (VI) fluoride exchange
triarylbenzenes
β-arylethenesulfonyl fluorides

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