Electrochemically Induced Michael Addition Reaction: An Overview

Abstract

Due to its high potential for the formation of carbon‐carbon bonds, Michael addition reaction is one of the closest reactions to the heart of synthetic organic chemists. Electrochemistry presents a very stimulating and divergent resource for selective oxidation and reduction in organic chemistry, generating activated species, for example radical anions or radical cations. In this review, we try to underscore usefulness of electrogenerated Michael addition reaction with the hope of encouraging synthetic organic chemists to contemplate it, as an efficient and green strategy when it is required in their designed multi‐step reaction pathways.

Visualization system based on hierarchical targeting for diagnosis and treatment of hepatocellular carcinoma

“…The required reaction conditions is mild and simple. Several FDA-approved antibody-drug adducts have been clinically obtained using such reactions [ 41 , 42 ]. Therefore, the Michael addition reaction is used in this study to attach the SNF peptide/EpCAM antibody to the corresponding nanoparticle shell and observed using CLSM.…”

Electrocatalytic Oxidative Transformation of Organic Acids for Carbon–Heteroatom and Sulfur–Heteroatom Bond Formation

“…In the same year, they also reported the synthesis of N ‐[4‐(dimethylamino)phenyl]benzenesulfonamide through the electrochemical reduction of NDA with arylsulfinic acids as nucleophiles (Scheme ) . This is the first report describing the generation of a Michael acceptor through electrochemical reduction …”

A selected small molecule prevents inflammatory osteolysis through restraining osteoclastogenesis by modulating PTEN activity

“…16 Interestingly, Michael acceptor system molecules can regulate numerous signal transduction pathways or enzymatic activities in cells through covalent binding with cysteine or arginine residues and then initiate the Michael addition reaction to exert anti-inflammatory or antioxidant functions. 17 Thus, we synthesized many compounds based on the structure of heclin and compared their potential biological activities. 16,18 In the present study, we performed further investigation by selecting a small molecule (compound 17) that acts as the most similar inhibitor of the HECT domain and could inhibit RANKL-induced osteoclastogenesis by attenuating NF-κB signalling and the formation of the NLRP3 inflammasome by regulating the ubiquitination of PTEN.…”

“…Heclin also exhibits the obvious basic structure of the Michael acceptor system, which also belongs to compound of acrylamide 16 . Interestingly, Michael acceptor system molecules can regulate numerous signal transduction pathways or enzymatic activities in cells through covalent binding with cysteine or arginine residues and then initiate the Michael addition reaction to exert anti‐inflammatory or antioxidant functions 17 . Thus, we synthesized many compounds based on the structure of heclin and compared their potential biological activities 16,18 …”