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Tandem [4 + 2]/[2 + 2] cycloaddition reactions involving indene or benzofurans and arynes.

Authors
  • Bhojgude, Sachin Suresh
  • Thangaraj, Manikandan
  • Suresh, Eringathodi
  • Biju, Akkattu T
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jul 03, 2014
Volume
16
Issue
13
Pages
3576–3579
Identifiers
DOI: 10.1021/ol501579d
PMID: 24964225
Source
Medline
License
Unknown

Abstract

The reaction of arynes with indene/benzofurans has been developed. The arynes were generated from 2-(trimethylsilyl)aryl triflates by the fluoride-induced 1,2-elimination react with indene or various benzofurans proceeding via a cascade reaction involving the Diels-Alder reaction and a [2 + 2] cycloaddition reaction. The tandem process afforded functionalized dihydrobenzocyclobutaphenanthrenes in moderate to good yields. Moreover, the method has been utilized for the one-pot synthesis of benzo[b]fluoranthene.

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