α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents: Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization

Kyalo Stephen Kanyiva, Daisuke Hamada, Sohei Makino, Hideaki Takano, Takanori Shibata

研究成果: Article査読

9 被引用数 (Scopus)

抄録

We developed a silver-catalyzed strategy for the generation of sulfonyl radicals from sulfonamides derived from α-amino acids. The reaction proceeded via a decarboxylation, N–S bond cleavage and radical cyclization sequence and allows the difunctionalization of alkynes and the synthesis of 3-sulfonylated coumarins. The reaction tolerated a broad scope of substrates and functional groups and could be extended to the synthesis of oxindoles and an isoquinolinedione by the capturing of the sulfonyl radical with an alkene moiety. Moreover, the proposed mechanism was supported experimentally and by DFT calculations.

本文言語English
ページ(範囲)5905-5909
ページ数5
ジャーナルEuropean Journal of Organic Chemistry
2018
43
DOI
出版ステータスPublished - 2018 11 25

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

フィンガープリント 「α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents: Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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