Electrochemical Oxidative [4+2] Annulation for the pi-Extension of Unfunctionalized Heterobiaryl Compounds

作者:Hu, X (Hu, Xia)[ 1 ] ; Nie, L (Nie, Lei)[ 1 ] ; Zhang, GT (Zhang, Guoting)[ 1 ] ; Lei, AW (Lei, Aiwen)[ 1 ]

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

卷: 59 期: 35 页: 15238-15243

DOI: 10.1002/anie.202003656

出版年: AUG 24 2020

在线发表日期: JUN 2020

文献类型:Article

摘要

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 pi-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.

关键词

作者关键词:annulation; heteroarenes; radical cations; synthetic methods; pi-extension

KeyWords Plus:C-H FUNCTIONALIZATION; DIELS-ALDER REACTIONS; AROMATIC-COMPOUNDS; INDOLES; ALKYNES; ELECTROSYNTHESIS; CYCLOADDITION; HETEROARENES; CYCLIZATION; CARBAZOLES

作者信息

通讯作者地址:

Wuhan University Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Peoples R China.

通讯作者地址: Lei, AW (通讯作者)

Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Peoples R China.

地址:

[ 1 ]‎ Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Peoples R China

电子邮件地址:aiwenlei@whu.edu.cn