Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
Angew Chem Int Ed Engl. 2019 Oct 14;58(42):15041-15045. doi: 10.1002/anie.201907269. Epub 2019 Sep 5.
A protocol for the three-component 1,4-carboamination of dienes is described. Synthetically versatile Weinreb amides were coupled with 1,3-dienes and readily available dioxazolones as the nitrogen source using [Cp*RhCl ] -catalyzed C-H activation to deliver the 1,4-carboaminated products. This transformation proceeds under mild reaction conditions and affords the products with high levels of regio- and E-selectivity. Mechanistic investigations suggest an intermediate Rh -allyl species is trapped by an electrophilic amidation reagent in a redox-neutral fashion.
描述了一种用于三组分 1,4-碳酰胺化二烯的方案。使用 [Cp*RhCl ]-催化的 C-H 活化,将合成多功能的 Weinreb 酰胺与 1,3-二烯和易得的二氧杂环戊酮(作为氮源)偶联,以提供 1,4-碳酰胺化产物。该转化在温和的反应条件下进行,并以高区域和 E-选择性获得产物。机理研究表明,中间 Rh-烯丙基物种以氧化还原中性的方式被亲电酰胺化试剂捕获。