4.8 Article

Gold-Catalyzed Deacylative Cycloisomerization Reactions of 3-Acylindole/ynes: A New Approach for Carbazole Synthesis

Journal

ORGANIC LETTERS
Volume 13, Issue 15, Pages 3786-3789

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol2012154

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Funding

  1. National Natural Science Foundation of China [20872163, 20732008, 20821002]
  2. Chinese Academy of Science
  3. Major State Basic Research Development Program [2011CB808700]

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The synthesis of functionalized carbazoles through gold-catalyzed deacylative cycloisomerization of 3-acylindole/ynes is described. A mechanistic proposal for these transformations involving a novel carbonyl group facilitated heterolytic fragmentation upon the loss of an acylium ion intermediate is presented. The eliminated acylium ion species could be trapped by the organogold intermediate to afford acylcarbazoles.

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