Regioselective/electro-oxidative intermolecular [3+2] annulation for the preparation of indolines

作者:Wang, QQ (Wang, Qingqing)[ 1 ] ; Wang, P (Wang, Pan)[ 1 ] ; Gao, XL (Gao, Xinlong)[ 1 ] ; Wang, D (Wang, Dan)[ 1 ] ; Wang, SC (Wang, Shengchun)[ 1 ] ; Liang, XA (Liang, Xingan)[ 1 ] ; Wang, LW (Wang, Liwei)[ 1 ] ; Zhang, H (Zhang, Heng)[ 1 ] ; Lei, AW (Lei, Aiwen)[ 1,2 ]

CHEMICAL SCIENCE

卷: 11 期: 8 页: 2181-2186

DOI: 10.1039/c9sc05729c

出版年: FEB 28 2020

文献类型:Article

摘要

Compared with the reported intramolecular electro-oxidative cyclization of alkenyl amines or vinyl anilines for the preparation of pyrrolidines or indolines, the intermolecular version is less studied. Herein, this electrochemical intermolecular oxidative annulation of anilines and alkenes for the preparation of indolines proceeded under external oxidant-free conditions. The most noteworthy achievement of our work is the facile generation of indolines with quaternary centers at the 2-position. In addition, alkenes and anilines bearing various functional groups can be well tolerated. Remarkably, electrolyte-free conditions were used in an electrochemical flow cell, which shows the application potential of this method.

关键词

KeyWords Plus:C-H ACTIVATION; ELECTROCHEMICAL-OXIDATION; ASYMMETRIC HYDROGENATION; BOND FORMATION; CYCLIZATION; ACCESS; FUNCTIONALIZATION; ANILINES; ALKENES; GENERATION

作者信息

通讯作者地址:

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

Jiangxi Normal University Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China.

通讯作者地址: Zhang, H; Lei, AW (通讯作者)

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

通讯作者地址: Lei, AW (通讯作者)

Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China.

地址:

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

[ 2 ]‎ Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China

电子邮件地址:hengzhang@whu.edu.cn; aiwenlei@whu.edu.cn