Litcius/Paper detail

Electrochemical Oxidative [4+2] Annulation for the π‐Extension of Unfunctionalized Heterobiaryl Compounds

Xia Hu, Lei Nie, Guoting Zhang, Aiwen Lei

2020Angewandte Chemie International Edition69 citationsDOI

Abstract

Considering their unique electronic properties and diverse biological activities, regioselective access to fused aromatic compounds is significantly important in the field of organic materials and pharmaceutical science. Herein, we developed electrochemical oxidative [4+2] annulation reactions of heterobiaryl compounds with alkynes or alkenes, leading to the formation of several polycyclic heteroaromatic compounds. This electrosynthetic methodology serves for the straightforward π-extension of unfunctionalized heterobiaryl compounds. The requirements of additional oxidants and prefunctionalization of starting materials are obviated. Through the in situ generation of heterobiaryl radical cation intermediates, various fused aromatic compounds were obtained with good yields and excellent regioselectivity.

Topics & Concepts

RegioselectivityAnnulationChemistryElectrochemistryCombinatorial chemistryOxidative phosphorylationOrganic chemistryCatalysisElectrodeBiochemistryPhysical chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques