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配体对钯催化的α,β-不饱和酮与(杂)芳基卤化物的位点选择性α-和γ-芳基化反应的控制

Ligand Control of Palladium-Catalyzed Site-Selective α- and γ-Arylation of α,β-Unsaturated Ketones with (Hetero)aryl Halides.

作者信息

Yuen On Ying, So Chau Ming

机构信息

Department of Applied Biology and Chemical Technology and State Key Laboratory of Chemical Biology and Drug Discovery, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, Hong Kong.

The Hong Kong Polytechnic University Shenzhen Research Institute, Shenzhen, P. R. China.

出版信息

Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23438-23444. doi: 10.1002/anie.202010682. Epub 2020 Nov 5.

Abstract

This study describes the first palladium-catalyzed, site-selective α- and γ-arylation of α,β-unsaturated ketones with (hetero)aryl halides. A wide range of hetero(aryl)halides coupled with α,β-unsaturated ketones, and transformation into the arylated products proceeded with excellent to good yields. The site selectivity of the reaction is switchable by simply changing the phosphine ligand to access either α-arylated or γ-arylated products in good to excellent yields by using a low catalyst loading, and the method demonstrates good functional-group compatibility.

摘要

本研究描述了首例钯催化的α,β-不饱和酮与(杂)芳基卤化物的位点选择性α-和γ-芳基化反应。多种(杂)芳基卤化物与α,β-不饱和酮发生偶联反应,并以优异至良好的产率转化为芳基化产物。通过简单地改变膦配体,该反应的位点选择性是可切换的,从而能够以低催化剂负载量、良好至优异的产率获得α-芳基化或γ-芳基化产物,并且该方法显示出良好的官能团兼容性。

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