Copper catalyzed Heck-like cyclizations of oxime esters
Copper catalyzed Heck-like cyclizations of oxime esters
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DOI：
10.1039/c4sc00652f
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发表时间：
2014-01-01
期刊：
影响因子：
8.4
通讯作者：
Bower, John F.
中科院分区：
文献类型：
--
作者：
Faulkner, Adele;Race, Nicholas J.;Bower, John F.
研究了铜催化的肟酯Heck环化反应。机理研究表明，通过生成和环化的中间体，具有亚胺基自由基的字符进行的反应途径。据我们所知，这项工作包括铜催化的氮杂-赫克反应的第一个例子，通过在氮氧化引发进行，以产生含有新烯烃的产品。这一新协议也是Pd基系统的有效替代品，并突出了用更便宜、更可持续的变体取代贵金属催化剂的价值。
Copper catalyzed Heck-like cyclizations of oxime esters are described. Mechanistic studies indicate a reaction pathway that proceeds via the generation and cyclization of an intermediate that possesses iminyl radical character. To the best of our knowledge, this work encompasses the first examples of Cu-catalyzed aza-Heck reactions that proceed via oxidative initiation at nitrogen to generate products containing a new alkene. This new protocol is also an effective alternative to Pd-based systems and highlights the value of replacing precious metal catalysts with cheaper and more sustainable variants.