Uniting Amide Synthesis and Activation by PIII/PV–Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines,Journal of the American Chemical Society

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Uniting Amide Synthesis and Activation by PIII/PV–Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-09-03 , DOI: 10.1021/jacs.1c07608
Jeffrey M Lipshultz ₁ , Alexander T Radosevich ₁

Affiliation

An organophosphorus (P^III/P^V redox) catalyzed method for the three-component condensation of amines, carboxylic acids, and pyridine N-oxides to generate 2-amidopyridines via serial dehydration is reported. Whereas amide synthesis and functionalization usually occur under divergent reaction conditions, here a phosphetane catalyst (together with a mild bromenium oxidant and terminal hydrosilane reductant) is shown to drive both steps chemoselectively in an auto-tandem catalytic cascade. The ability to both prepare and functionalize amides under the action of a single organocatalytic reactive intermediate enables new possibilities for the efficient and modular preparation of medicinal targets.

中文翻译：

通过 PIII/PV 催化的串联缩合结合酰胺合成和活化：2-酰胺基吡啶的三组分组装

报道了一种有机磷（P ^III /P ^V氧化还原）催化胺、羧酸和吡啶N-氧化物三组分缩合通过连续脱水生成 2-氨基吡啶的方法。虽然酰胺合成和官能化通常发生在不同的反应条件下，但此处显示膦烷催化剂（与温和的溴氧化剂和末端氢硅烷还原剂一起）在自动串联催化级联中以化学选择性驱动这两个步骤。在单一有机催化活性中间体的作用下制备和官能化酰胺的能力为高效和模块化制备药物靶标提供了新的可能性。

更新日期：2021-09-15

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