Preparation of 2-Amino-5-homoallylfurans via Palladium-Catalyzed Tandem Cycloisomerization/Heck-Type Coupling of Homoallenyl Amides with Allyltrialkylsilanes
作者:Jian Zhang、Mingchang Wu、Wei Lu、Shuaifeng Wang、Yan Zhang、Cungui Cheng、Gangguo Zhu
DOI:10.1021/acs.joc.7b02131
日期:2017.10.20
cycloisomerization/Heck-type coupling between homoallenyl amides and allyltrialkylsilanes, using a novel DDQ/MnO2 combination as the efficient oxidant. The reaction exclusively affords γ-allylation products in good to excellent yields with broad substrate scope under exceptionally mild reaction conditions. It represents one of the rare examples of the Pd-catalyzed intermolecular Heck-type coupling of allytrialkylsilanes
使用新颖的DDQ / MnO 2组合作为有效的氧化剂,通过钯催化的均戊烯基酰胺和烯丙基三烷基硅烷之间的串联双环异构化/ Heck型偶联,已经实现了直接接触2-氨基-5-全烯丙基呋喃。在异常温和的反应条件下,该反应以优异的产率独家提供了良好的γ-烯丙基化产物,并且具有广泛的底物范围。它代表了由P-硅烷基消除终止的Pd催化的烯丙基三烷基硅烷的分子间Heck型偶联的稀有例子之一,因此由于出色的γ-选择性而补充了传统的烯丙基化方法。