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Copper-Catalyzed C-H Cyanation of Terminal Alkynes with Cyanogen Iodide

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

*Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Email:,

K. Okamoto, M. Watanabe, N. Sakata, M. Murai, K. Ohe, Org. Lett., 2013, 15, 5810-5813.

DOI: 10.1021/ol402863g (free Supporting Information)


A copper-catalyzed reaction of terminal alkynes with cyanogen iodide (ICN) produces alkynyl cyanides in the presence of of tetramethylpiperidine as a sterically congested base. 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.

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Key Words

cyanation, alkynylation

ID: J54-Y2013