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无过渡金属催化的α-芳基酮的C-C σ键活化及随后的锌催化分子内环化反应:四取代呋喃的合成

Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans.

作者信息

Yuan Yang, Tan Hailu, Kong Lingkai, Zheng Zhong, Xu Murong, Huang Jiaqi, Li Yanzhong

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering East China Normal University, 500 Dongchuan Road, China.

出版信息

Org Biomol Chem. 2019 Mar 6;17(10):2725-2733. doi: 10.1039/c9ob00081j.

Abstract

A highly atom-economical protocol for the synthesis of tetrasubstituted furans has been developed. This process is realized through the tandem reactions of Cs2CO3 promoted C-C σ-bond activation of α-aryl ketones followed by Zn-catalyzed intramolecular cyclization. This represents the first example for the preparation of tetrasubstituted furans through rearrangement of molecular skeletons and subsequent transformations. Mild reaction conditions and readily accessible starting materials make the protocol attractive in organic synthesis.

摘要

已经开发出一种用于合成四取代呋喃的高原子经济性方法。该过程通过碳酸铯促进的α-芳基酮的C-C σ键活化的串联反应,随后进行锌催化的分子内环化来实现。这代表了通过分子骨架重排及后续转化制备四取代呋喃的首个实例。温和的反应条件和易于获得的起始原料使得该方法在有机合成中颇具吸引力。

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