Metal-Free Aminoiodination of Alkynes Under Visible Light Irradiation for the Construction of a Nitrogen-Containing Eight-Membered Ring System

Stephen Kyalo Kanyiva, Tane Marina, Shun Nishibe, Takanori Shibata

Research output: Contribution to journalArticlepeer-review

Abstract

A method for the synthesis of dihydrodibenzo[c,e]azocine derivatives via a regioselective intramolecular aminoiodination of alkynes under visible light irradiation has been developed. This protocol uses a combination of iodine and hypervalent iodine to realize a sulfonamidyl radical, followed by intramolecular addition to alkyne to form a vinyl radical. Subsequent trapping of iodine radical affords an 8-membered heterocycle. Applications of the obtained iodinated 8-membered heterocycles in the Suzuki-Miyaura coupling and deiodination are also demonstrated. (Figure presented.).

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusAccepted/In press - 2021

Keywords

  • Alkynes; Dibenzazocines
  • Aminoidodination
  • Hypervalent Iodine
  • Metal-Free Synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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