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铜催化自由基芳基迁移方法制备氰基磺酰基氧化吲哚/氰基烷基酰胺。

Copper-Catalyzed Radical Aryl Migration Approach for the Preparation of Cyanoalkylsulfonylated Oxindoles/Cyanoalkyl Amides.

机构信息

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China.

出版信息

Org Lett. 2021 Feb 5;23(3):751-756. doi: 10.1021/acs.orglett.0c03973. Epub 2021 Jan 21.

Abstract

A copper-catalyzed radical cross-coupling of oxime esters and activated alkenes is accomplished for the synthesis of cyanoalkylsulfonylated oxindoles and cyanoalkyl amides via an aryl migration strategy. Specifically, the subsequent mechanism research indicates that the unique desulfonylation and sulfone addition processes were involved in the transformation. This transformation is identified as having good functional group applicability with two different quaternary stereocenter in a regioselective manner, which is controlled by the substituent group of the nitrogen.

摘要

铜催化肟酯与活化烯烃的自由基交叉偶联反应,通过芳基迁移策略,实现了氰基烷基磺酰化吲哚啉和氰基烷基酰胺的合成。具体而言,后续的机理研究表明,该转化涉及独特的脱磺酰基和砜加成过程。该转化具有良好的官能团适用性,在区域选择性方面控制两个不同的季立体中心,受氮取代基的影响。

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