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亲电磷烯配合物对烯酮的分子内活化以构建2-磷杂呋喃。

Intramolecular Activation of Enones by Electrophilic Phosphinidene Complexes to Construct 2-Phosphafurans.

作者信息

Li Hong, Tian Rongqiang, Duan Zheng

机构信息

College of Chemistry, International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, Green Catalysis Center, Zhengzhou University, Zhengzhou 450001, P. R. China.

出版信息

Org Lett. 2022 Jan 21;24(2):767-770. doi: 10.1021/acs.orglett.1c04281. Epub 2022 Jan 10.

Abstract

Herein, we report a facile and highly atom-economic approach to 2-phosphafurans by using simple 2-chloroethylphosphine and acetylenic ketones. The key step of this protocol utilizes the Lewis acidity of electrophilic phosphinidenes to induce an intramolecular cyclization with enones. Dearomative hetero-Diels-Alder reactions of 2-phosphafurans provide two series of bicyclic phosphacycles. This rare synthetic application of Lewis acidity of electrophilic phosphinidene complexes represents a new frontier of phosphinidene chemistry.

摘要

在此,我们报道了一种通过使用简单的2-氯乙基膦和炔酮来制备2-磷杂呋喃的简便且高度原子经济的方法。该方案的关键步骤利用亲电磷叶立德的路易斯酸性来诱导与烯酮的分子内环化。2-磷杂呋喃的去芳构化杂Diels-Alder反应提供了两个系列的双环磷环。亲电磷叶立德配合物路易斯酸性的这种罕见的合成应用代表了磷叶立德化学的一个新前沿。

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