中国化学快报(英文版)2024,Vol.35Issue(7) :35-53.DOI:10.1016/j.cclet.2023.109322

Beyond 1,4-addition of in-situ generated(aza-)quinone methides and indole imine methides

Yan-Li Li Zhi-Ming Li Kai-Kai Wang Xiao-Long He
中国化学快报(英文版)2024,Vol.35Issue(7) :35-53.DOI:10.1016/j.cclet.2023.109322

Beyond 1,4-addition of in-situ generated(aza-)quinone methides and indole imine methides

Yan-Li Li 1Zhi-Ming Li 2Kai-Kai Wang 3Xiao-Long He2
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作者信息

  • 1. Medical College,Xinxiang University,Xinxiang 453000,China
  • 2. School of Food and Bioengineering,Xihua University,Chengdu 610039,China
  • 3. School of Pharmacy,Xinxiang University,Xinxiang 453000,China
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Abstract

The conjugate addition of in-situ generated(aza-)quinone methides(QMs)and indole imine methides(IIMs)emerged as a powerful protocol to access densely functionalized benzenes and indoles.Hydrox-ybenzyl alcohols,aminobenzhydryl alcohols,and varied indolylmethanols served as most effective pre-cursors for the in-situ generation of such reactive species under acid conditions.The relevant propargylic alcohol has proven to be an elegant precursor to generate the propargylic-QMs and-IIMs via the acid promoted dehydration process,thus enabling diverse challenging remote activation to proceed conjugate 1,6-and 1,8-additions.Moreover,the heteroarene has proven to be workable to transfer the LUMO of the p-QMs and 2-IIMs,thus inducing the remote nucleophilic dearomative additions.The conjugate additions of(aza-)p-QMs and varied IIMs has made significant contribution in the field of remote activation chem-istry in past decade.This review summarizes the latest advances of the remote conjugate additions of the in-situ generated QMs and IIMs.

Key words

Conjugate addition/QMs/IIMs/LUMO/Remote activation/Dearomative addition

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基金项目

National Natural Science Foundation of China(22001216)

Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province(CSPC202315)

Science and Technology Department of Sichuan Province,China(2022NSFSC1203)

Higher Education Institution Key Research Project Plan of Henan Province(24B150031)

Program for Youth Backbone Teacher Training in University of Henan Province(2021GGJS163)

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

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影响因子:0.771
ISSN:1001-8417
参考文献量121
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