4.7 Article

Photoinduced Intramolecular Cyclization of o-Ethenylaryl Isocyanides with Organic Disulfides Mediated by Diphenyl Ditelluride

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 10, Pages 3880-3887

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo200299d

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan [19350095]
  2. Tohoku University
  3. Japan Society for the Promotion of Science (JSPS)
  4. Grants-in-Aid for Scientific Research [19350095] Funding Source: KAKEN

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Photoinduced reaction of o-ethenylaryl isocyanides with organic disulfides in the presence of diphenyl ditellurides affords the corresponding bisthiolated indole derivatives via a radical cyclization process. The cyclization can proceed at room temperature upon visible-light irradiation and exhibits good tolerance to functional groups. Several organic disulfides also can be employed for this cyclization, and the corresponding bisthiolated indole derivatives are obtained selectively. In addition, the photoinduced reaction of o-ethenylaryl isocyanides with bis(2-aminophenyl) disulfide affords tetracyclic compounds in one portion.

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