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螺[苯并呋喃-2,2'-呋喃]-3-酮的可扩展非对映选择性电合成

Scalable Diastereoselective Electrosynthesis of Spiro[benzofuran-2,2'-furan]-3-ones.

作者信息

Yavari Issa, Shaabanzadeh Sina, Ghafouri Kiyana

机构信息

Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran 1463694571, Iran.

出版信息

J Org Chem. 2024 Jan 5;89(1):425-432. doi: 10.1021/acs.joc.3c02186. Epub 2023 Dec 12.

Abstract

Spirobenzofuran scaffolds, because of their three-dimensional structure, are incorporated into several valuable natural products and drug candidate molecules. Herein, with the assistance of electrosynthesis, we introduce a novel electrochemical approach for achieving spirobenzofurans in a user-friendly and operationally simple undivided cell setup under constant current. This metal-catalyst-free electrochemical procedure afforded spiro[benzofuran-2,2'-furan]-3-ones with high diastereoselectivity. Compatibility with gram-scale synthesis along with the convenient accessibility of reaction instruments and starting materials collectively raised the importance of this protocol compared to previous challenging methods. Furthermore, mechanistic cognizance of this reaction is obtained by the investigation of the cyclic voltammetry spectra of reactants.

摘要

螺苯并呋喃骨架因其三维结构,被纳入多种有价值的天然产物和候选药物分子中。在此,在电合成的辅助下,我们引入了一种新颖的电化学方法,在恒流下于用户友好且操作简单的无隔膜电解槽装置中实现螺苯并呋喃的合成。这种无金属催化剂的电化学方法以高非对映选择性得到了螺[苯并呋喃 -2,2'-呋喃]-3-酮。与克级规模合成的兼容性以及反应仪器和起始原料的便捷可得性,相较于先前具有挑战性的方法,共同提升了该方法的重要性。此外,通过研究反应物的循环伏安光谱获得了该反应的机理认识。

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