Rhodium(III)-Catalyzed Switchable β-C(sp2)–H Alkenylation and Alkylation of Acyclic Enamides with Allyl Alcohols,Organic Letters

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Rhodium(III)-Catalyzed Switchable β-C(sp2)–H Alkenylation and Alkylation of Acyclic Enamides with Allyl Alcohols
Organic Letters ( IF 4.9 ) Pub Date : 2024-04-19 , DOI: 10.1021/acs.orglett.4c01234
Xiaolan Li _{1,

2} , Jie Liu ₂ , Ruixin Song ₂ , Xuzhong Luo _{1,

2} , Haiqing Luo ₂

Affiliation

Herein, rhodium(III)-catalyzed β-C(sp²)–H alkenylation and alkylation of enamides are presented using readily accessible allylic alcohols by switching the reaction conditions. This tunable transformation has been applied to a wide range of substrates and typically proceeded with excellent regioselectivity and stereoselectivity as well as with good functional group tolerance. The catalytic system offers an efficient approach for synthesizing various functionalized enamides bearing N-(2Z,4E)-butadiene and (Z)-β-C(sp²)–H alkylated enamides. In addition, mechanistic experiments suggest that Rh(III)-catalyzed C–H activation is not related to the critical step.

中文翻译：

铑(III)催化的无环烯酰胺与烯丙醇的可转换β-C(sp2)–H烯基化和烷基化

在此，通过切换反应条件，使用易于获得的烯丙醇，提出了铑(III)催化的β-C(sp ² )–H烯基化和烯酰胺烷基化。这种可调谐的转化已应用于多种底物，并且通常具有优异的区域选择性和立体选择性以及良好的官能团耐受性。该催化系统提供了一种有效的方法来合成带有N- (2 Z ,4 E )-丁二烯和( Z )-β-C(sp ² )–H烷基化烯酰胺的各种官能化烯酰胺。此外，机理实验表明，Rh(III) 催化的 C-H 活化与关键步骤无关。

更新日期：2024-04-19

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