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通过碳钯化/硼化/逆狄尔斯-阿尔德串联反应实现钯催化的()-烯基硼的多组分组装。

Palladium-Catalyzed Multicomponent Assembly of ()-Alkenylborons via Carbopalladation/Boronation/Retro-Diels-Alder Cascade Reaction.

作者信息

Zhang Yuqing, Chen Yanhui, Tian Qingyu, Wang Binju, Cheng Guolin

机构信息

Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, China.

State Key Laboratory of Physical Chemistry of Solid Surfaces and Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry, College of Chemistry and Chemical Engineering and Innovation Laboratory for Sciences and Technologies of Energy Materials of Fujian Province (IKKEM), Xiamen University, Xiamen 361005, China.

出版信息

J Org Chem. 2023 Aug 18;88(16):11793-11800. doi: 10.1021/acs.joc.3c01084. Epub 2023 Jul 29.

Abstract

A palladium-catalyzed multicomponent cascade reaction of aryl iodides, oxanorbornadiene, and diborns to access ()-alkenylborons is reported. This transformation proceeds through the sequential carbopalladation/boronation/retro-Diels-Alder domino reaction. The oxanorbornadiene used in this reaction serves as an acetylene surrogate, which is generated via a retro-Diels-Alder reaction. Such a stereoselective and scalable approach has a wide range of functional group tolerance and good substrate universality.

摘要

报道了一种钯催化的芳基碘化物、氧杂降冰片二烯和双环戊二烯的多组分串联反应,用于合成()-烯基硼。该转化过程通过顺序的碳钯化/硼化/逆狄尔斯-阿尔德多米诺反应进行。此反应中使用的氧杂降冰片二烯作为乙炔替代物,通过逆狄尔斯-阿尔德反应生成。这种立体选择性且可扩展的方法具有广泛的官能团耐受性和良好的底物通用性。

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