4.7 Article

Gold-Catalyzed Cascade Friedel-Crafts/Furan-Yne Cyclization/Heteroenyne Metathesis for the Highly Efficient Construction of Phenanthrene Derivatives

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 2-3, Pages 392-400

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000644

Keywords

annulation; cascade reactions; gold catalysis; heteroenyne metathesis; phenanthrene

Funding

  1. National Natural Science Foundation of China [20872163, 20732008, 20821002]
  2. Chinese Academy of Science, Science and Technology Commission of Shanghai Municipality [08QH14030]
  3. Major State Basic Research Development Program [2006CB806105]

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A rapid access to highly substituted phenanthrenyl ketones through gold-catalyzed cyclization of 1,6-diyn-4-en-3-ols with furans has been developed. Gold catalysts are effective to catalyze three cascade processes involving Friedel-Crafts/furan-yne cyclization/heteroenyne metathesis through C-O bond and alkyne activation. This method offers several advantages such as high selectivities and easily accessible starting materials.

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