催化作用
卡宾
氧离子
螺旋桨烷
化学
亚甲基
环丁烷
亲核细胞
乙醚
组合化学
光化学
键裂
有机化学
双环分子
戒指(化学)
离子
作者
Seungyong Shin,Yuhyun Kim,Sungwoo Hong
标识
DOI:10.1021/acscatal.3c03681
摘要
In this study, we report an innovative Ag(I)-catalyzed carbene transfer reaction that employs [1.1.1]propellane as a precursor to form the methylene cyclobutyl carbene complex for a controllable three-component reaction. The key strategy of this method involves the formation of Ag-bound oxonium ions as intermediates, which are generated by the reaction between the Ag-carbene complex and cyclic ether-type solvents such as THF and 1,4-dioxane. The subsequent nucleophile-induced C–O bond cleavage leads to a three-component etherification of methylene cyclobutane. Employing this strategy, we successfully coupled various amine and alcohol partners, demonstrating the method’s potential for the late-stage functionalization of intricate, biologically relevant molecules and synthetic manipulations of the resulting products. To further explore the mechanism driving selective three-component reactions, we have conducted comprehensive experimental and computational studies.
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