Versatile Electrochemical Oxidative C(sp₂)−H Bond Selenylation of Resveratrol

Abstract

A simple and environmentally benign procedure for electrochemical oxidative mono-and bis-selenylation of the resveratrol C(sp 2 )À H bond was developed. Driven by galvanostatic electrolysis in an undivided cell, it provided efficient transformation under oxidant-, base-, and transition metal-free conditions, in an open system at room temperature. With satisfactory functional group compatibility, it required a substoichiometric amount of NaI, which acted as an electrolyte and mediator.

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“…The regioselective electrochemical oxidation employed resulted in the corresponding isolated selenylated products in moderate to good yields. Later on, Mendes and co-workers [55] described the functionalization of resveratrol 54 through an efficient environmentally benign procedure (Scheme 26). The unprecedented mono-and bis-selenylated compounds 55 and 56 were achieved in the absence of transition metal, oxidant and base, under air, using NaI as electrolyte and different diselenides 6 as a selenium source.…”

Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp2)–H and C(sp3)–H bonds

“…In the same year, Mendes and coworkers disclosed an electrochemical oxidative mono- and diselenylation of resveratrol 137 with various di(hetero)aryl/dialkyl/dibenzyl diselenides 39 in an open system at room temperature (Scheme 46). 233 The reactions were performed under oxidant-, base- and transition-metal-free conditions using platinum and graphite as electrodes and a substoichiometric amount of NaI as an electrolyte and mediator. It is worth mentioning that the diselenylation process required increased amounts of diselenides and NaI, and an extended reaction time using graphite instead of platinum as the cathode.…”

Continuous flow reactions in the preparation of active pharmaceutical ingredients and fine chemicals

“…Recently, electrochemistry has received renewed attention as a versatile approach in synthetic organic chemistry. [89][90][91][92] Its unique ability to generate highly reactive radical intermediaries under mild conditions has inspired the emergence of various innovative methodologies for the preparation of valuable chemical products. 93 The use of continuous flow conditions for synthetic electrochemical reactions offers several advantages compared to more traditional batch conditions.…”