Base-promoted direct E-selective olefination of organoammonium salts with sulfones toward stilbenes and conjugated 1,3-dienes.

Tao Zhang, Runji Wang, Jiani Chen, Long Liu, Tianzeng Huang, Chunya Li, Zhi Tang, Tieqiao Chen

Organic & biomolecular chemistry 2022 Jun 01

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A base-promoted direct deaminative olefination of organoammonium salts was developed. Only mediated by KOtBu, a series of benzyl and cinnamyl ammonium salts reacted smoothly with sulfones, producing the valuable stilbenes and related 1,3-diene derivatives in good to high yields with good functional group tolerance and excellent E-selectivity. With this developed method, biologically active resveratrol and DMU-212 were also successfully prepared, which further demonstrates the practicality of this reaction.

Citation

Tao Zhang, Runji Wang, Jiani Chen, Long Liu, Tianzeng Huang, Chunya Li, Zhi Tang, Tieqiao Chen. Base-promoted direct E-selective olefination of organoammonium salts with sulfones toward stilbenes and conjugated 1,3-dienes. Organic & biomolecular chemistry. 2022 Jun 01;20(21):4369-4375