S-acetals) under mild conditions. Simple treatment of such enaminones with PhI(OAc)2 at ambient temperature in air afforded diverse multiply functionalized α,β-unsaturated amides including β-cyclopropylated acrylamides, in which a wide array of functional groups such as aryl, (hetero)aryl, alkenyl, and alkyl can be conveniently introduced to a ketene moiety. The reaction mechanism was investigated by exploring
酰胺键的形成是有机合成,药物开发和材料科学领域最重要的转变之一。对于有机
化学家而言,酰胺的有效构建一直是最具挑战性的任务。在这里,我们报告了在温和的条件下,在烷
硫基官能化的烯胺酮(α-氧代
乙烯酮N,S-
乙缩醛)中通过邻位基团迁移协助形成酰胺键(-CONH-)的简明方法。用PhI(OAc)2简单处理此类烯胺酮在环境温度下,在空气中可得到多种多重官能化的α,β-不饱和酰胺,包括β-环丙基化的
丙烯酰胺,其中各种官能团(例如芳基,(杂)芳基,烯基和烷基)可以方便地引入烯酮部分。通过探索酰胺氧和碳原子的起源以及反应中间体的分离和结构表征,研究了反应机理。酰胺键形成反应也可以在无溶剂机械研磨条件下有效地进行。