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  4. Synthesis of Benzo[a]carbazoles through Visible Light-Induced Cycloaromatization
 
research article

Synthesis of Benzo[a]carbazoles through Visible Light-Induced Cycloaromatization

Yao, Bo  
•
Wang, Qian  
•
Zhu, Jieping  
June 29, 2020
Helvetica Chimica Acta

We report herein a synthesis of 5,6-diarylbenzo[a]carbazoles by a sequence of 6 pi-electrocyclization followed by beta-elimination. The highly functionalized 2,3-disubstituted indoles used for this cycloaromatization process are prepared by Pd-catalyzed cyclizative cross-coupling ofortho-alkynylanilines withortho-alkynylbenzamides. The combination of these two reactions allows us to develop a facile synthesis of benzo[a]carbazoles directly from two easily accessible internal alkynes without isolation of the indole intermediates.

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Type
research article
DOI
10.1002/hlca.202000106
Web of Science ID

WOS:000543806700001

Author(s)
Yao, Bo  
Wang, Qian  
Zhu, Jieping  
Date Issued

2020-06-29

Publisher

WILEY-V C H VERLAG GMBH

Published in
Helvetica Chimica Acta
Volume

103

Issue

8

Article Number

e2000106

Subjects

Chemistry, Multidisciplinary

•

Chemistry

•

benzo[a]carbazole

•

indoles

•

cycloaromatization

•

visible light

•

electrocyclic reactions

•

elimination

•

ortho-alkynylanilines

•

h functionalization

•

palladium

•

alkynes

•

insertion

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
July 9, 2020
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/169922
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