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Electrochemical Oxidative [4+2] Annulation for the π‐Extension of Unfunctionalized Heterobiaryl Compounds
Author(s) -
Hu Xia,
Nie Lei,
Zhang Guoting,
Lei Aiwen
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202003656
Subject(s) - regioselectivity , annulation , chemistry , electrochemistry , combinatorial chemistry , oxidative phosphorylation , organic chemistry , catalysis , electrode , biochemistry
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.