4.8 Article

Gold-Catalyzed Annulation/Fragmentation: Formation of Free Gold Carbenes by Retro-Cyclopropanation

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 34, Pages 11881-11883

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja104743k

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Funding

  1. MICINN [CTQ2010-16088/BQU, CSD2006-0003]
  2. AGAUR [SGR 47]
  3. ICIQ Foundation

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The gold(I)-catalyzed cyclization of 1-(prop-2-yn-1-yl)-2-alkenylbenzenes substituted at the benzylic position with OR groups gives 1,3-disubstituted naphthalenes with concomitant fragmentation of the alkene. One of these annulations proceeds by a retro-cyclopropanation that leads to free gold(I) carbenes.

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