Photoinduced 1,2-Hydro(cyanomethylation) of Alkenes with a Cyanomethylphosphonium Ylide

Tomoya Miura, Daisuke Moriyama, Yuuta Funakoshi, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

An efficient method has been developed for the 1,2-hydro(cyanomethylation) of alkenes, in which a cyanomethyl radical species is generated from a cyanomethylphosphonium ylide by irradiation with visible light in the presence of an iridium complex, a thiol, and ascorbic acid. The cyanomethyl radical species then adds across the C=C double bond of an alkene to form an elongated alkyl radical species that accepts a hydrogen atom from the thiol to produce an elongated aliphatic nitrile. The ascorbic acid acts as the reductant to complete the catalytic cycle.

Original languageEnglish
Pages (from-to)511-514
Number of pages4
JournalSynlett
Volume30
Issue number4
DOIs
Publication statusPublished - 2019
Externally publishedYes

Keywords

  • alkenes
  • hydro(cyanomethylation)
  • nitriles
  • phosphonium ylides
  • photocatalysis
  • radicals

ASJC Scopus subject areas

  • Organic Chemistry

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