Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros 07-01, Singapore 138665.
J Org Chem. 2012 Sep 21;77(18):8007-15. doi: 10.1021/jo301252c. Epub 2012 Aug 30.
A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide.
一种实用的方法，用于将醛与经济的氯化铵或胺盐酸盐进行酰胺化，以使用廉价的硫酸铜或氧化亚铜作为催化剂和叔丁基过氧化氢水溶液作为氧化剂，合成各种酰胺。该酰胺化反应操作简单，在温和条件下，利用廉价且易得的试剂，大多数情况下可得到良好至优秀的产率，得到伯、仲和叔酰胺。从游离胺原位形成胺盐可扩展反应的底物范围。手性酰胺也可从其相应的手性胺合成，而没有可检测到的外消旋化。这种酰胺形成反应的实用性已在抗心律失常药物 N-乙酰普鲁卡因胺的有效合成中得到证明。
