Microwaves and Aqueous Solvents Promote the Reaction of Poorly Nucleophilic Anilines with a Zincke Salt
作者:Narimane Zeghbib、Paul Thelliere、Michael Rivard、Thierry Martens
DOI:10.1021/acs.joc.6b00208
日期:2016.4.15
engaged in Zincke reactions. Efficient transformations were obtained, even when conducted on electronically deactivated, eventually also sterically hindered, substrates. This was achieved by the combined use of microwave activation and aqueous solvents. Under our conditions, the role of water revealed indeed crucial to avoid the self-degradation of the Zincke salt, the reagent of the reaction.
Zincke反应可将伯胺转化为各自的N-烷基化或N-芳基吡啶鎓盐。虽然亲核伯胺(通常是脂肪族伯胺)通常会导致定量反应,并且已经有大量文献证明,但不良亲核胺的使用仍需要深入研究。迄今为止,胺的亲核性缺乏是重新抑制的。本文涉及的主题是一系列已参与Zincke反应的衍生自苯胺的伯胺。即使在电子失活的,最终也是空间受阻的底物上进行,也可以获得有效的转化。这是通过结合使用微波活化和水性溶剂来实现的。在我们的条件下,水的作用确实显示对于避免反应试剂辛克盐的自降解至关重要。