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光氧化还原/钴卟啉协同催化胺和磺酰肼与烯烃的烯丙基化反应,以获得α-烯丙基胺和烯丙基砜。

Photoredox/cobaloxime co-catalyzed allylation of amines and sulfonyl hydrazines with olefins to access α-allylic amines and allylic sulfones.

机构信息

Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, and Chemistry and Chemical Engineering Guangdong Laboratory, Shantou, Guangdong 515063, P. R. China.

出版信息

Org Biomol Chem. 2021 Oct 6;19(38):8227-8231. doi: 10.1039/d1ob01307f.

Abstract

Herein, we reported a dual-catalytic platform for the allylation of amines and sulfonyl hydrazines with olefins to selectively access α-allylic amines and allylic sulfones in good yields by combining photoredox catalysis and cobaloxime catalysis. This strategy avoided the use of a stoichiometric amount of terminal oxidant and the use of pre-functionalized allylic precursors, representing a green and ideal atom- & step-economical process. Good substrate scope and gram-scale synthesis demonstrated the utility of this protocol. Mechanistic studies revealed that a radical process is probably involved in this reaction.

摘要

在这里,我们报告了一种双催化平台,用于通过结合光氧化还原催化和钴卟啉催化,将胺和磺酰腙与烯烃进行烯丙基化反应,以高收率选择性地合成α-烯丙基胺和烯丙基砜。该策略避免了使用化学计量的终端氧化剂和使用预官能化的烯丙基前体,代表了一种绿色和理想的原子经济性和步骤经济性过程。良好的底物范围和克级规模合成证明了该方案的实用性。机理研究表明,该反应可能涉及自由基过程。

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