Synthesis of alkyl sulfones from alkenes and tosylmethylphosphonium iodide through photo-promoted cc bond formation

Tomoya Miura, Daisuke Moriyama, Sho Miyakawa, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

Abstract

A new synthetic method for alkyl sulfones through CC bond formation between alkenes and tosylmethylphosphonium iodide is reported. A tosylmethyl radical is generated from the phosphonium iodide under irradiation of visible light with the aid of fac-Ir(ppy)3. It undergoes regioselective 1,2-addition across the carboncarbon double bond to afford an elongated alkyl radical, which abstracts a hydrogen atom from C6F5SH, producing an alkyl sulfone with one-carbon extension.

Original languageEnglish
Pages (from-to)1382-1385
Number of pages4
JournalChemistry Letters
Volume49
Issue number11
DOIs
Publication statusPublished - Nov 2020
Externally publishedYes

Keywords

  • Phosphonium salts
  • Radicals
  • Sulfones

ASJC Scopus subject areas

  • Chemistry(all)

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