Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
J Am Chem Soc. 2011 Nov 16;133(45):18018-21. doi: 10.1021/ja208162w. Epub 2011 Oct 21.
Pyridines, which comprise one of the most important classes of the six-membered heterocyclic compounds, are widely distributed in nature, and the transition-metal-catalyzed [2 + 2 + 2] cycloaddition reaction of two alkynes and a nitrile is one of the most powerful methods for preparing versatile, highly substituted pyridine derivatives. However, the lack of chemo- and regioselectivity is still a crucial issue associated with fully intermolecular [2 + 2 + 2] cycloaddition. The present study developed the Ni(0)-catalyzed intermolecular dehydrogenative [4 + 2] cycloaddition reaction of 1,3-butadienes with nitriles to give a variety of pyridines regioselectively.
吡啶是六元杂环化合物中最重要的一类，广泛存在于自然界中，过渡金属催化的两个炔烃和一个腈的[2 + 2 + 2]环加成反应是制备多功能、高取代吡啶衍生物的最有效方法之一。然而，化学和区域选择性的缺乏仍然是完全分子间[2 + 2 + 2]环加成相关的一个关键问题。本研究开发了 Ni(0)催化的 1,3-丁二烯与腈的分子间脱氢[4 + 2]环加成反应，以高区域选择性地得到各种吡啶。
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