Sc(OTf)3-catalyzed synthesis of anhydrides from twisted amides
Sc(OTf)3-catalyzed synthesis of anhydrides from twisted amides
复制标题
Sc(OTf)3 催化扭曲酰胺合成酸酐
DOI：
10.1039/c7ob00086c
复制
发表时间：
2017
影响因子：
3.2
通讯作者：
Szostak Michal
中科院分区：
文献类型：
--
作者：
Liu Yongmei;Liu Ruzhang;Szostak Michal
报道了一种由扭曲的酰胺合成酸酐的新方法。采用Sc(OTf)3催化剂，在无外加亲核剂的情况下，由酰胺类化合物一步合成了酸酐。机理研究表明，催化剂的配位对诱导具有挑战性的N-C活化步骤至关重要。这一过程进一步突出了扭曲的酰胺在有机合成中的用途。值得注意的是，反应表明，在所开发的条件下，基于戊二酰亚胺支架的扭曲酰胺比羧酸酐更具活性，这为通过酰胺N-C键断裂进行可控的顺序催化打开了大门。
A novel synthesis of anhydrides from twisted amides is reported. Sc(OTf)3 catalysis in the presence of water is used to synthesize anhydrides in one step from amides without external nucleophiles. Mechanistic studies indicate that the coordination of the catalyst is critical to induce the challenging N–C activation step. This process further highlights the utility of twisted amides in organic synthesis. Notably, the reaction indicates that twisted amides based on the glutarimide scaffold are more reactive than carboxylic acid anhydrides under the developed conditions, which opens the door to controlled sequential catalysis through amide N–C bond cleavage.