Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols

Chi Ma, Youlai Zhang*, Huan Zhang, Junru Li, Yasuhiro Nishiyama, Hiroki Tanimoto, Tsumoru Morimoto, Kiyomi Kakiuchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

A new and efficient thiochromenone S,S-dioxide-based photolabile protecting group for propargylic alcohols is described. Robust protection reactions were developed through copper (II)-catalyzed substitution of propargylic alcohols. Subsequent photodeprotection proceeded smoothly to give the corresponding propargylic alcohols quantitatively within 15 minutes, as demonstrated by 1H NMR spectroscopy and HPLC. Notably, the photoproduct derived from the thiochromenone derivatives showed a high fluorescence quantum yield, permitting monitoring of the reaction progress by fluorescence spectroscopy. A new strategy for the synthesis of triazoles by a one-pot reaction is also presented.

Original languageEnglish
Article numberst-2016-w0578-l
Pages (from-to)560-564
Number of pages5
JournalSynlett
Volume28
Issue number5
DOIs
StatePublished - 2017/03/15

Keywords

  • photodeprotection
  • photolabile groups
  • propargylic alcohols
  • protecting group
  • thiochromenone dioxides
  • triazoles

ASJC Scopus subject areas

  • Organic Chemistry

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