Easy Access to 1-Amino and 1-Carbon Substituted Isoquinolines via Cobalt-Catalyzed CH/NO Bond Activation

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• 作者：Krishnamoorthy Muralirajan ; Ramajayam Kuppusamy ; Sekar Prakash and Chien-Hong Cheng
• 关键词：alkynes ; annulation ; CH activation ; cobalt ; isoquinolines ; oximes
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：March 3, 2016
• 年：2016
• 卷：358
• 期：5
• 页码：774-783
• 全文大小：613K
• ISSN：1615-4169

文摘

A green atom-economical method for the synthesis of highly functionalized 1-amino and 1-carbon substituted isoquinolines from the reaction of N′-hydroxybenzimidamides and aryl ketoximes, respectively, with alkynes via pentamethylcyclopentadienylcobalt(III)-catalyzed CH/NO bond activation is described. The external oxidant-free annulation reaction uses the =NOH moiety in N′-hydroxybenzimidamides or N-aromatic ketone oximes as the directing group and internal oxidant. This first row transition metal-catalyzed annulation serves as an efficient alternative for the synthesis of isoquinolines, as water is the only by-product and expensive noble metals such as rhodium(III), iridium(III), palladium(II), and ruthenium(II) are not required. The reaction proceeds via CH activation, alkyne insertion, reductive elimination, and NO activation.