67231-26-9Relevant academic research and scientific papers
Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles
Liu, Peiye,Clark, Ronald J.,Zhu, Lei
, p. 5092 - 5103 (2018/05/15)
A new method to convert terminal alkynes under relatively mild conditions to 1-cyanoalkynes using in situ formed cyanogen is described. 1-Cyanoalkynes have a higher reactivity than terminal alkynes in the ruthenium(II)-catalyzed regiospecific azide-alkyne cycloaddition to afford 4-cyano-1,2,3-triazoles. A mechanistic proposal different from the one that terminal alkynes adopt under the same reaction conditions is proposed. This work provides a new and convenient two-step sequence to prepare 4-cyano-1,2,3-triazoles from terminal alkynes and organic azides.
Silver-Mediated Direct C-H Cyanation of Terminal Alkynes with N-Isocyanoiminotriphenylphosphorane
Wang, Hannan,Mi, Pengbing,Zhao, Wanjun,Kumar, Ravi,Bi, Xihe
supporting information, p. 5613 - 5616 (2017/10/25)
A direct cyanation of terminal alkynes for the synthesis of propionitrile derivatives, with the aid of silver salt using water additive, has been achieved. The cyano source used is N-isocyanoiminotriphenylphosphorane, which is nontoxic, safe, and easy to handle. This protocol is characterized by its operational simplicity, high efficiency with excellent yields, broad substrate scope, and greater functional group tolerance.
Alkynylcyanation of alkynes and dienes catalyzed by nickel
Hirata, Yasuhiro,Tanaka, Masaaki,Yada, Akira,Nakao, Yoshiaki,Hiyama, Tamejiro
experimental part, p. 5037 - 5050 (2009/11/30)
Alkynyl cyanides are found to add across alkynes and 1,2-dienes in the presence of a catalyst prepared in situ from Ni(cod)2, xantphos, and BPh3. A range of functionalized conjugated cis-enynes are obtained with high regioselectivity. The addition reaction across norbornadiene proceeds in the absence of BPh3 to give exo-cis adduct exclusively. A stoichiometric reaction of an alkynyl cyanide, Ni(cod)2, xantphos, and BPh3 gives trans-(xantphos)Ni(CNBPh3)(C{triple bond, long}CSiMe2t-Bu), which is suggested to be a plausible reaction intermediate of the alkynylcyanation reaction.
