Electrooxidation Enables Selective Dehydrogenative [4+2] Annulation between Indole Derivatives

作者:Song, CL (Song Chunlan)[ 1,2 ] ; Liu, K (Liu Kun)[ 1,2 ] ; Jiang, X (Jiang Xu)[ 1,2 ] ; Dong, X (Dong Xin)[ 1,2 ] ; Weng, Y (Weng Yue)[ 1,2 ] ; Chiang, CW (Chiang Chien-Wei)[ 1,2 ] ; Lei, AW (Lei Aiwen)[ 1,2,3 ]

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

卷: 59 期: 18 页: 7193-7197

DOI: 10.1002/anie.202000226

出版年: APR 27 2020

文献类型:Article

摘要

Dearomative annulation of indoles has emerged as a powerful tool for the preparation of polycyclic indoline-based alkaloids. Compared with well-established methods towards five-membered-ring-fused indolines, the six-membered-ring-fused indolines are rarely accessed under thermal conditions. Herein, a dearomative [4+2] annulation between different indoles is developed through an electrochemical pathway. This transformation offers a remarkably regio- and stereoselective route to highly functionalized pyrimido[5,4-b]indoles under oxidant- and metal-free conditions. Notably, this electrochemical approach maintains excellent functional-group tolerance and can be extended as a modification tactic for pharmaceutical research. Preliminary mechanism studies indicate that the electrooxidation annulation proceeds through radical-radical cross-coupling between an indole radical cation and an N-centered radical generated in situ.

关键词

作者关键词:[4+2] annulation; dearomative annulation; electrosynthesis; indole; pyrimido[5; 4-b]indoles

KeyWords Plus:RECENT PROGRESS; STRATEGIES; ELECTROCHEMISTRY; RADICALS

作者信息

通讯作者地址:

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

Wuhan University Wuhan Univ, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China.

Chinese Academy of Sciences Shanghai Institute of Organic Chemistry, CAS Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China.

通讯作者地址: Weng, Y; Chiang, CW; Lei, AW (通讯作者)

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

通讯作者地址: Weng, Y; Chiang, CW; Lei, AW (通讯作者)

Wuhan Univ, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China.

通讯作者地址: Lei, AW (通讯作者)

Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China.

地址:

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

[ 2 ]‎ Wuhan Univ, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China

[ 3 ]‎ Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

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