Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide

Kazuhiro Okamoto, Masahito Watanabe, Naoki Sakata, Masahito Murai, Kouichi Ohe

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Abstract

A copper-catalyzed reaction of terminal alkynes with cyanogen iodide (ICN) that produces alkynyl cyanides has been developed. The use of tetramethylpiperidine as a sterically congested base was successful in this reaction. Some control experiments revealed that the reaction involves the noncatalyzed formation of alkynyl iodides followed by copper-catalyzed cyanation of the iodides without the formation of copper(I) acetylide. This observation contrasts with what is normally observed in various copper-mediated reactions using terminal alkynes.

Original languageEnglish
Pages (from-to)5810-5813
Number of pages4
JournalOrganic Letters
Volume15
Issue number22
DOIs
Publication statusPublished - Nov 15 2013

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Okamoto, K., Watanabe, M., Sakata, N., Murai, M., & Ohe, K. (2013). Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide. Organic Letters, 15(22), 5810-5813. https://doi.org/10.1021/ol402863g