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Iodine-mediated cascade cyclization of enediynes to iodinated benzo[a]carbazoles.

Authors
  • Chen, Chin-Chau
  • Yang, Shyh-Chyun
  • Wu, Ming-Jung
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Dec 16, 2011
Volume
76
Issue
24
Pages
10269–10274
Identifiers
DOI: 10.1021/jo201795t
PMID: 22050791
Source
Medline
License
Unknown

Abstract

Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 1.2 equiv of iodine in CH(2)Cl(2) gave benzo[a]carbazoles (2) in good yields. Mechanistic studies showed this reaction must go through the haloindole (3) followed by iodonium ion catalyzed atom-transfer cyclization reaction to give the benzo[a]carbazoles.

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