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Palladium-Catalyzed Synthesis of α-Iminonitriles from Aryl Halides via Isocyanide Double Insertion Reaction

Zhen-Bang Chen, Ying Zhang, Qing Yuan, Fang-Ling Zhang, Yong-Ming Zhu* and Jing-Kang Shen*

*College of Pharmaceutical Sciences, Soochow University, Suzhou, 215123, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China, Email: zhuyongmingsuda.edu.cn, jkshenmail.shcnc.ac.cn

Z.-B. Chen, Y. Zhang, Q. Yuan, F.-L. Zhang, Y.-M. Zhu, J.-K. Shen, J. Org. Chem., 2016, 81, 1610-1616.

DOI: 10.1021/acs.joc.5b02777 (free Supporting Information)



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Abstract

A palladium-catalyzed double isocyanide insertion and elimination enables an efficient one-pot synthesis of α-iminonitriles from readily available aryl halides without using hypertoxic cyanides and excess oxidants. Furthermore, the utility of this reaction was demonstrated by a rapid total synthesis of a quinoxaline.

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Key Words

imines, nitriles


ID: J42-Y2016