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通过环酮肟酯 C-C 键断裂诱导的单电子转移 C(sp)-N 偶联。

Single-Electron-Transfer-Induced C(sp)-N Couplings via C-C Bond Cleavage of Cycloketoxime Esters.

机构信息

State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering , Nanjing University , Nanjing 210093 , China.

College of Science , Nanjing Forestry University , Nanjing 210037 , China.

出版信息

J Org Chem. 2019 Aug 16;84(16):10145-10159. doi: 10.1021/acs.joc.9b01338. Epub 2019 Aug 8.

Abstract

A practical single-electron-transfer-induced selective C(sp)-N coupling of cycloketoximes with anilines via C-C bond cleavage under copper-catalytic and synergetic photoredox/copper-catalytic reaction systems has been uncovered. These two powerful and simple protocols demonstrated excellent selectivity and good functional group compatibility without any base or ligand control. Preliminary mechanistic experiments indicated that a radical-mediated process was involved in these transformations.

摘要

通过铜催化和协同光氧化还原/铜催化反应体系,发现了一种实用的、基于单电子转移的环酮肟与苯胺的 C(sp)-N 偶联反应,该反应可通过 C-C 键断裂实现。这两种强大而简单的方案表现出优异的选择性和良好的官能团兼容性,无需任何碱或配体控制。初步的机理实验表明,这些转化涉及自由基介导的过程。

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