Electrochemical-Induced Transfer Hydrogenation of Imidazopyridines with Secondary Amine as Hydrogen Donor

Abstract

Electrochemical-induced transfer hydrogenation (TH) of N-heteroaromatic to construct biologically active functional molecule is an appealing and yet challenging task. We report herein the first selective transfer hydrogenation of imidazopyridine derivatives with secondary amines as the hydrogen donors under electrochemical conditions. The successful conversion of cathode transfer hydrogenation depends on the solvation effect. Importantly, such electrochemical-induced transfer hydrogenation can be easily amplified with excellent efficiency.

Electrochemical Ammonium Cation‐Assisted Hydropyridylation of Ketone‐Activated Alkenes: Experimental and Computational Mechanistic Studies

“…[7] We speculate the proton-rich ammonium salt can be simultaneously proton-coupled with ketone-activated alkenes and cyanopyridine to reduce their activation potential. In continuing our efforts in the electrochemical hydrogenation of unsaturated hydrocarbons, [8] we wish to report a simple, selective hydropyridylation of ketoneactivated alkenes assisted by NH 4…”

Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams

“…Under these mild conditions, the desired hydroxylactam 2a was isolated in 94% yield (entry 1). In comparison, reduced yields were obtained when the reaction conditions were modified in one of the following manners: changing the cathode to graphite (entry 2), changing the solvent to MeOH (entry 3) or CH 2 Cl 2 (entry 4), or using another base such as morpholine (entry 5), i -Pr 2 NEt (entry 6), or pyridine (entry 7) …”

Electrochemical‐Induced Hydrogenation of Electron‐Deficient Internal Olefins and Alkynes with CH3OH as Hydrogen Donor

“…Despite several achievements made so far, it is still an urgent task and challenge to develop efficient, convenient, easy to scale up, and environmentally friendly electrochemical strategies for the selective hydrogenation of electron‐deficient internal olefins and alkynes to synthesize ketones. In the continuation of our efforts in the transfer hydrogenation of imidazopyridines with secondary amine as hydrogen donor [8] and functionalization of alkenes, [9] here, we wish to report highly selective hydrogenation of electron‐deficient internal alkenes and alkynes access to the saturated ketone with inexpensive methanol serving as a proton donor. KSCN and Ph 2 S were selected as the anode parallel paired electrolysis reagents for hydrogenation of ketene dithioacetals and ynones, which can effectively inhibit the side reactions caused by oxidation of the substrate.…”