Synthesis of biphenyl-type and diarylether-type oligostilbenes from the biomimetic oxidation of cyano-resveratrol derivatives

Abstract

Two trans-cyanostilbene derivatives were prepared, and their oxidative dimerizations promoted by horseradish peroxidase-H₂O₂ were investigated. An M₅–M₅-coupled biphenyl-type dimer was first synthesized from the biomimetic oxidative coupling reaction of 8-cyano-resveratrol. A novel M₅–M_O-4-coupled diarylether-type dimer was obtained through the oxidation of 3,5-dibromo-8-cyano-resveratrol and the following debromination reaction. The cyano group at the C-8 of two cyano-stilbenes had obvious influences on the regioselectivity of their coupling reactions.

GRAPHICAL ABSTRACT

Keywords:

• Cyanostilbene
• resveratrol
• oxidative coupling
• diarylether
• biphenyl

Additional information

Funding

This research work was supported by ‘Science and technology program of Gansu province’ [No. 22JR5RA347].