Electrochemical oxidative C(sp(3))-H azolation of lactams under mild conditions

作者:Wan, ZH (Wan, Zhaohua)[ 1 ] ; Wang, D (Wang, Dan)[ 1 ] ; Yang, ZX (Yang, Zixuan)[ 1 ] ; Zhang, H (Zhang, Heng)[ 1 ] ; Wang, SC (Wang, Shengchun)[ 1 ] ; Lei, AW (Lei, Aiwen)[ 1 ]

GREEN CHEMISTRY

卷: 22 期: 12 页: 3742-3747

DOI: 10.1039/d0gc00687d

出版年: JUN 21 2020

文献类型:Article

摘要

Lactam-containing structural compounds are ubiquitous in drugs and biomolecules. An electrochemical oxidative direct C(sp(3))-H azolation of lactams has been reported under metal catalyst-free and external chemical oxidant-free conditions. This electrochemical C(sp(3))-H/N-H coupling is characterized by its broad substrate scope of azoles and lactams under mild conditions at room temperature. Mechanistic studies suggested that the reaction possibly involves a radical process. Moreover, the site selectivity can be explained by DFT calculations. More meaningfully, a gram-scale synthesis method of flow electrochemistry was employed to show the scaled-up applicability of this transformation.

关键词

KeyWords Plus:H BOND ADJACENT; METAL-FREE; C-N; ORGANOCATALYTIC AMINATION; GAMMA-LACTAMS; ETHERS; AZOLES; TETRAHYDROFURAN; ALKYLATION; ACTIVATION

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