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
Full Text: HTML
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 ...
Related Articles:
Facile conversion of carboxamides to nitriles
[Mai, Khuong; Patil, Ghanshyam Tetrahedron Letters, 1986 , vol. 27, # 20 p. 2203 - 2206]
One-pot synthesis of conjugated alkynenitriles from aldehydes
[Kim, Joong-Gon; Lee, Eun Hwa; Jang, Doo Ok Tetrahedron Letters, 2007 , vol. 48, # 13 p. 2299 - 2301]
[Synlett, , # 20 p. 3378 - 3382]
Copper??Catalyzed Oxidative Transformation of Aryl Propargylic Azides to Aryl Propiolonitriles
[Wang, Teng; Yin, Hang; Jiao, Ning Advanced Synthesis and Catalysis, 2013 , vol. 355, # 6 p. 1207 - 1210]
Generation and [3+ 2] cycloaddition reactions of oxazoline N-oxides
[Ashburn, Stephen P.; Coates, Robert M. Journal of Organic Chemistry, 1984 , vol. 49, p. 3127 - 3133]