Ph(O) group for protection of terminal acetylenes

Xin Yang, Daisuke Matsuo, Yoshinori Suzuma, Jing Kun Fang, Feng Xu, Akihiro Orita, Junzo Otera, Shingo Kajiyama, Nagatoshi Koumura, Kohjiro Hara

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

A protecting group Ph(O) for terminal ethyne was newly developed. This protecting group can be introduced readily to terminal ethyne by CuI-catalyzed phosphination and subsequent oxidation with H Ph(O)-protected ethynes remained intact in Sonogashira coupling, and their high polarity enabled easy separation of the desired coupling product from by-products. By treatment with t-BuOK, Ph(O)-protected ethynes were transformed to the corresponding terminal ethynes.

Original languageEnglish (US)
Article numberU04611ST
Pages (from-to)2402-2406
Number of pages5
JournalSynlett
Issue number16
DOIs
StatePublished - Sep 12 2011

Keywords

  • alkynes
  • coupling
  • phosphorylation
  • protecting groups

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