4.8 Article

Gold-catalyzed Bicyclization of Diaryl Alkynes: Synthesis of Polycyclic Fused indole and Spirooxindole Derivatives

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ORGANIC LETTERS
卷 20, 期 9, 页码 2733-2736

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00939

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资金

  1. National Natural Science Foundation of China
  2. NSFC of Jiangsu [NSFC21602148, BK20150315]

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An unprecedented gold-catalyzed bicyclization reaction of diaryl alkynes has been developed for the synthesis of indoles in good to high yields. Mechanistically, this alkyne bifunctionalization transformation was terminated by a stepwise formal X-H insertion reaction to furnish the corresponding polycyclic-frameworks with structural diversity, and the key intermediate 3H-indole was isolated and characterized for the first time. In addition, further transformation of these generated tetracyclic-indoles with PCC as the oxidant provided straightforward access to the spirooxindoles in high yields.

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