Improved efficiency of photo-induced synthetic reactions enabled by advanced photo flow technologies

Takahide Fukuyama, Takayoshi Kasakado, Mamoru Hyodo, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

In this article, we discuss how effective photo-induced organic reactions became when applied evolving photo flow technologies through our experiences over these two last decades. We started with the flow update of traditional [2 + 2] cycloaddition using Mikroglas Dwell device as a flow reactor and a compact light source, such as blacklight, instead of a high-pressure mercury lamp. Then we examined Barton nitrite reaction using a photo flow reactor consisting of stainless-steel channels and a quartz glass top provided by DNS. Again the use of blacklight was successful. However, the energy profile of these reactions was improved further by the use of LED lights. We used a photo-flow set-up, consisting of stainless steel engraved microchannels covered by a quartz top (MiChS L-1) and a sodium lamp, for the isomerization of a fulleroid to PCBM. Photo-redox-catalyzed alkene alkylation proceeded within a shortened reaction time when the same photo flow reactor and white LED were used instead of a batch reactor. Photo-induced reductive 5-exo-dig radical cyclization and reduction of alkenyl halides proceeded smoothly, thanks to the combination of a photo flow reactor and low-pressure Hg lamp. We also applied flow technologies for photo-bromination and chlorination of C–H bonds. Photocatalytic oxidation of benzyl alcohol by molecular oxygen became quick when high-power LED irradiation was employed. Graphical abstract: [Figure not available: see fulltext.]

Original languageEnglish
JournalPhotochemical and Photobiological Sciences
DOIs
StateAccepted/In press - 2022

Keywords

  • Barton nitrite reaction
  • C-H halogenation
  • C-H oxidation
  • Cossy radical cyclization
  • Photo flow reactor
  • Photoisomerization
  • Photoredox-catalyzed alkylation
  • Radical reduction
  • [2 + 2] Cycloaddition

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