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Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes.

Authors
  • Naoe, Saori
  • Suzuki, Yamato
  • Hirano, Kimio
  • Inaba, Yusuke
  • Oishi, Shinya
  • Fujii, Nobutaka
  • Ohno, Hiroaki
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Jun 01, 2012
Volume
77
Issue
11
Pages
4907–4916
Identifiers
DOI: 10.1021/jo300771f
PMID: 22568806
Source
Medline
License
Unknown

Abstract

The gold-catalyzed cascade intermolecular addition-intramolecular carbocyclization reaction of dialkynylbenzenes was developed. In this reaction, regioselective addition of an external nucleophile toward the terminal alkyne and subsequent 6-endo-dig cyclization proceeded to give the 1,3-disubstituted naphthalenes in good yields. The direct synthesis of disubstituted chrysenes via a gold-catalyzed addition and double cyclization cascade using a triyne-type substrate was also achieved.

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