Red-light-mediated BartonMcCombie reaction

Akihiro Ogura, Naoki Ichii, Kouhei Shibata, Ken Ichi Takao

Research output: Contribution to journalArticlepeer-review

Abstract

A red-light-mediated BartonMcCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative.

Original languageEnglish
Pages (from-to)936-941
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume93
Issue number7
DOIs
Publication statusPublished - 2020 Jul

Keywords

  • Barton–McCombie reaction
  • Chlorophyll a
  • Red light

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Red-light-mediated BartonMcCombie reaction'. Together they form a unique fingerprint.

Cite this