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无外部氧化剂条件下,用邻苯甲酰基羟胺对不饱和酮肟的未活化烯烃进行氨苯甲酰氧基化反应。

External-oxidant-free amino-benzoyloxylation of unactivated alkenes of unsaturated ketoximes with O-benzoylhydroxylamines.

机构信息

State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China.

School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Shandong, Yantai, 264005, China.

出版信息

Chem Commun (Camb). 2021 May 25;57(42):5215-5218. doi: 10.1039/d1cc01565f. Epub 2021 Apr 28.

Abstract

A new copper-catalyzed two-component amino-benzoyloxylation of unactivated alkenes of unsaturated ketoximes with O-benzoylhydroxylamines as the benzoyloxy sources is developed. Chemoselectivity of this method toward amino-benzoyloxylation or oxy-benzoyloxylation of alkenyl ketoximes relies on the position of the tethered olefins, and provides an external-oxidant-free alkene difunctionalization route that directly utilizes O-benzoylhydroxylamines as the benzoyloxy radical precursors and internal oxidants for the divergent synthesis of cyclic nitrones and isoxazolines.

摘要

开发了一种新的铜催化的不饱和酮肟的未活化烯烃的双组分氨基苯甲酰氧基化反应,其中 O-苯甲酰羟胺作为苯甲酰氧基源。该方法对烯基酮肟的氨基苯甲酰氧基化或氧苯甲酰氧基化的化学选择性取决于连接烯烃的位置,并提供了一种无外部氧化剂的烯烃双官能化途径,直接利用 O-苯甲酰羟胺作为苯甲酰氧基自由基前体和内部氧化剂,用于环状硝酮和异噁唑啉的发散合成。

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