Visible‐Light‐Induced Intramolecular Double Dearomative Cycloaddition of Arenes

Herein we report visible‐light‐induced intramolecular double dearomative cycloaddition of arenes. Compared with the well‐known photodimerization of arenes under ultraviolet irradiation, the current reactions are carried out under mild conditions and feature wide substrate scope. A large array of str...

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Published inAngewandte Chemie International Edition Vol. 60; no. 13; pp. 7036 - 7040
Main Authors Zhu, Min, Xu, Hao, Zhang, Xiao, Zheng, Chao, You, Shu‐Li
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 22.03.2021
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
arene
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
Cycloaddition
dearomatization
indole
Irradiation
photocatalysis
Physical Sciences
Science & Technology
Stereoselectivity
Substrates
Ultraviolet radiation
indole
arene
dearomatization
CATALYTIC ASYMMETRIC DEAROMATIZATION
PHOTODIMERIZATION
PHOTOREACTIONS
cycloaddition
AZETIDINES
RECENT PROGRESS
photocatalysis
PHOTOCYCLOADDITION REACTIONS
PHOTOCHEMICAL-REACTIONS
TRANSFORMATIONS
ANTHRACENES
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Abstract Herein we report visible‐light‐induced intramolecular double dearomative cycloaddition of arenes. Compared with the well‐known photodimerization of arenes under ultraviolet irradiation, the current reactions are carried out under mild conditions and feature wide substrate scope. A large array of structurally‐diverse polycyclic indoline derivatives is afforded in high yields (up to 98 %) with exclusive diastereoselectivity (>20:1 dr) via dearomative [4+2] or [2+2] pathway. The visible‐light‐induced intramolecular double dearomative cycloaddition of arenes is reported. The reactions are carried out under mild conditions and feature a wide substrate scope. A large array of polycyclic indoline derivatives is afforded via dearomative [4+2] or [2+2] cycloaddition pathways in high yields with exclusive diastereoselectivity.
AbstractList Herein we report visible-light-induced intramolecular double dearomative cycloaddition of arenes. Compared with the well-known photodimerization of arenes under ultraviolet irradiation, the current reactions are carried out under mild conditions and feature wide substrate scope. A large array of structurally-diverse polycyclic indoline derivatives is afforded in high yields (up to 98 %) with exclusive diastereoselectivity (>20:1 dr) via dearomative [4+2] or [2+2] pathway.Herein we report visible-light-induced intramolecular double dearomative cycloaddition of arenes. Compared with the well-known photodimerization of arenes under ultraviolet irradiation, the current reactions are carried out under mild conditions and feature wide substrate scope. A large array of structurally-diverse polycyclic indoline derivatives is afforded in high yields (up to 98 %) with exclusive diastereoselectivity (>20:1 dr) via dearomative [4+2] or [2+2] pathway.
Herein we report visible‐light‐induced intramolecular double dearomative cycloaddition of arenes. Compared with the well‐known photodimerization of arenes under ultraviolet irradiation, the current reactions are carried out under mild conditions and feature wide substrate scope. A large array of structurally‐diverse polycyclic indoline derivatives is afforded in high yields (up to 98 %) with exclusive diastereoselectivity (>20:1 dr) via dearomative [4+2] or [2+2] pathway.
Herein we report visible‐light‐induced intramolecular double dearomative cycloaddition of arenes. Compared with the well‐known photodimerization of arenes under ultraviolet irradiation, the current reactions are carried out under mild conditions and feature wide substrate scope. A large array of structurally‐diverse polycyclic indoline derivatives is afforded in high yields (up to 98 %) with exclusive diastereoselectivity (>20:1 dr) via dearomative [4+2] or [2+2] pathway. The visible‐light‐induced intramolecular double dearomative cycloaddition of arenes is reported. The reactions are carried out under mild conditions and feature a wide substrate scope. A large array of polycyclic indoline derivatives is afforded via dearomative [4+2] or [2+2] cycloaddition pathways in high yields with exclusive diastereoselectivity.
Author Zhang, Xiao
Zheng, Chao
Xu, Hao
Zhu, Min
You, Shu‐Li
Author_xml – sequence: 1
  givenname: Min
  surname: Zhu
  fullname: Zhu, Min
  organization: ShanghaiTech University
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  givenname: Hao
  surname: Xu
  fullname: Xu, Hao
  organization: ShanghaiTech University
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  givenname: Xiao
  surname: Zhang
  fullname: Zhang, Xiao
  email: zhangxiao@sioc.ac.cn
  organization: Fujian Normal University
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  givenname: Chao
  orcidid: 0000-0002-7349-262X
  surname: Zheng
  fullname: Zheng, Chao
  email: zhengchao@sioc.ac.cn
  organization: Chinese Academy of Sciences
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  orcidid: 0000-0003-4586-8359
  surname: You
  fullname: You, Shu‐Li
  email: slyou@sioc.ac.cn
  organization: ShanghaiTech University
BackLink https://www.ncbi.nlm.nih.gov/pubmed/33449427$$D View this record in MEDLINE/PubMed
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Issue 13
Keywords indole
arene
dearomatization
CATALYTIC ASYMMETRIC DEAROMATIZATION
PHOTODIMERIZATION
PHOTOREACTIONS
cycloaddition
AZETIDINES
RECENT PROGRESS
photocatalysis
PHOTOCYCLOADDITION REACTIONS
PHOTOCHEMICAL-REACTIONS
TRANSFORMATIONS
ANTHRACENES
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Snippet Herein we report visible‐light‐induced intramolecular double dearomative cycloaddition of arenes. Compared with the well‐known photodimerization of arenes...
Herein we report visible-light-induced intramolecular double dearomative cycloaddition of arenes. Compared with the well-known photodimerization of arenes...
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SubjectTerms arene
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
Cycloaddition
dearomatization
indole
Irradiation
photocatalysis
Physical Sciences
Science & Technology
Stereoselectivity
Substrates
Ultraviolet radiation
Title Visible‐Light‐Induced Intramolecular Double Dearomative Cycloaddition of Arenes
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202016899
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https://www.ncbi.nlm.nih.gov/pubmed/33449427
https://www.proquest.com/docview/2501877098
https://www.proquest.com/docview/2478589254
Volume 60
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