Organic letters

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

K Okamoto, M Watanabe, N Sakata, M Murai…

Index: Okamoto, Kazuhiro; Watanabe, Masahito; Sakata, Naoki; Murai, Masahito; Ohe, Kouichi Organic Letters, 2013 , vol. 15, # 22 p. 5810 - 5813

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Citation Number: 12

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 ...