α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents

Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization

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

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2018 Jan 1

Fingerprint

Coumarins
Cyclization
Sulfonamides
Silver
reagents
amino acids
silver
Amino Acids
Alkynes
Alkenes
synthesis
Discrete Fourier transforms
Functional groups
decarboxylation
alkynes
alkenes
cleavage
Substrates
oxindole
Decarboxylation

Keywords

  • Amino acids
  • Coumarins
  • Oxindoles
  • Silver
  • Sulfonamides

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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abstract = "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.",
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language = "English",
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T1 - α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents

T2 - Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization

AU - Kanyiva, Stephen Kyalo

AU - Hamada, Daisuke

AU - Makino, Sohei

AU - Takano, Hideaki

AU - Shibata, Takanori

PY - 2018/1/1

Y1 - 2018/1/1

N2 - 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.

AB - 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.

KW - Amino acids

KW - Coumarins

KW - Oxindoles

KW - Silver

KW - Sulfonamides

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