4.7 Article

Synthesis of Polysubstituted Furans through Electrochemical Selenocyclization of Homopropargylic Alcohols

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 22, Pages 16084-16094

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01688

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Funding

  1. CSIR
  2. SERB, DST, India [CRG/2020/006021]
  3. IISER Kolkata

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The mild and efficient electrochemically driven synthetic route allows for the access of polysubstituted selenofuran derivatives through diselenide-promoted cyclization of homopropargyl alcohols, with up to 84% isolated yield. This methodology demonstrates good functional group compatibility and further conversion to valuable furan derivatives.
The current method represents an electrochemi-cally driven synthetic route to access polysubstituted selenofuran derivatives through the diselenide-promoted cyclization of homopropargyl alcohols. The tandem electro-oxidative trans-formation operates at ambient temperature and in the absence of an external oxidant. This mild and efficient methodology exhibits good functional group compatibility, providing a broad range of substrate scopes up to 84% isolated yield. Further conversion of the seleno-functionality afforded other valuable furan derivatives.

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