Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides

Kyalo Stephen Kanyiva, Kanako Uchida, Takanori Shibata

Research output: Contribution to journalReview articlepeer-review

Abstract

We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound. The mechanism studies are conducted using radical scavengers and deuterated toluene.

Original languageEnglish
Pages (from-to)1377-1384
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume94
Issue number4
DOIs
Publication statusPublished - 2021

Keywords

  • Amino acids
  • C-H sulfonylation
  • Radicals

ASJC Scopus subject areas

  • Chemistry(all)

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