N-Iodosuccinimide in Oxidative Dimerization of Methyl Cinnamates

Herein the reaction of methy cinnamates with N-Iodosuccinimide (NIS) is reported and the possible formation of dihydrobenzofuryl dimeric derivatives (DHBF), known for their biological activities, is explored. Having an oxidizing capacity, we studied the behavior of NIS with methyl ferulate and under optimized reaction conditions we obtained its DHBF dimer in 35% yield. It is worth to note that we did not obtain the DHBF in his natural form, but rather as the demethylated compound, likely due to dismutation reactions activated by the presence of water in the solvent. Methyl caffeate reacted with NIS to furnish the DHBF dimer in 15% yield, while methyl coumarate and methyl isoferulate did not give any form of DHBF dimers, showing the importance of a hydroxyl group in para position on an activated system and an electron-rich aromatic ring. An electrochemical investigation by cyclic voltammetry was carried out on the three cinnamates and confirmed the correlation between dimerization and oxidation potential: methyl ferulate and methyl caffeate dimerize, while methyl coumarate, due to its higher oxidizing potential, does not. Herein the reaction of N-iodosuccinimide with different cinnamates was reported: methyl ferulate furnished its dihydrobenzofuran (DHBF) dimer up to 35% yield, although in its demethylated form, methyl caffeate 15% yield, while methyl coumarate none. Their electrochemical behavior was studied by cyclic voltammetry and the correlation with the oxidizing potential of the substrates was found. image