Precise manipulation of electron transfers to enable the site-selective hydropyridylation of ynones

Abstract

Precise manipulation of electron transfers for site-selective hydropyridylation of ynones for β-pyridyl ketones and pyridinated propargyl alcohols synthesis tends to be an attractive strategy but remains a challenging task. Herein,...

Electrosynthesis of N/S-heterocycles

“…This method demonstrates controllable electron transfers, exceptional regioselectivity, facile gram-scale synthesis, and environmentally benign characteristics (Scheme 14). 29 In order to clearly explore the mechanism of the reaction, we carried out the square wave voltammetry (SWV) and kinetic experiments (Scheme 15A and B). The SWV technique was employed to accurately and rapidly identify the electron transfer processes involved in the hydropyridinylation of ynones (Scheme 15A(a)), thereby facilitating the elucidation of the reaction mechanism.…”

“…This method demonstrates controllable electron transfers, exceptional regioselectivity, facile gram-scale synthesis, and environmentally benign characteristics (Scheme 14). 29…”

Visible-Light-Induced Acylative Pyridylation of Styrenes

“…6 Wen's subsequent work revealed another innovative electrochemical hydropyridylation approach for α,β-unsaturated ketones, including enones 7 and ynones (Scheme 1b). 8 Nonetheless, the development of efficient three-component coupling methods, particularly those incorporating styrene�a globally produced industrial staple exceeding 37 million tons in 2022�remains a critical need. Styrene's affordability and global availability have prompted chemists to investigate its wide application, especially on difunctionalization.…”

“…Over the past two years, Jiang and Qiao’s group developed an innovative blue-light-mediated reductive coupling of chalcone with cyanopyridines, catalyzed by dicyanopyrazine (Scheme b) . Wen’s subsequent work revealed another innovative electrochemical hydropyridylation approach for α,β-unsaturated ketones, including enones and ynones (Scheme b) . Nonetheless, the development of efficient three-component coupling methods, particularly those incorporating styrenea globally produced industrial staple exceeding 37 million tons in 2022remains a critical need.…”