4.8 Article

Gold(I)-Catalyzed Tandem Cyclization-Selective Migration Reaction of 1,3-Dien-5-ynes: Regioselective Synthesis of Highly Substituted Benzenes

Journal

ORGANIC LETTERS
Volume 13, Issue 18, Pages 4970-4973

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202129n

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Funding

  1. Ministerio de Ciencia e Innovacion (MICINN)
  2. FEDER [CTQ2010-15358, CTQ2009-09949/BQU]
  3. Junta de Castilla y Leon [BU021A09, GR-172]

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Highly substituted benzene derivatives have been easily prepared in a regioselective way from readily available 1,3-hexadien-5-ynes through a gold(I)-catalyzed tandem reaction. The process involves an initial cyclization followed by a selective Wagner-Meerwein shift in which the migration preference seems to be determined by the ability to stabilize a positive charge.

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