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铑(III)催化的各种非环烯酰胺与芳基硅烷的直接 C-H 芳基化反应。

Rhodium(III)-Catalyzed Direct C-H Arylation of Various Acyclic Enamides with Arylsilanes.

机构信息

Department of Chemistry & Chemical Engineering, Gannan Normal University, Ganzhou 341000, China.

Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, China.

出版信息

Org Lett. 2021 Jan 1;23(1):31-36. doi: 10.1021/acs.orglett.0c03578. Epub 2020 Dec 18.

Abstract

The stereoselective β-C(sp)-H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by the gram-scale synthesis and further elaboration of the product. In addition, Rh(III)-catalyzed C-H activation is considered to be the critical step in the reaction mechanism.

摘要

通过 Rh(III)催化的交叉偶联反应,展示了各种无环烯酰胺与芳基硅烷的立体选择性β-C(sp)-H 芳基化反应。该方法具有高效和立体选择性、广泛的底物范围、良好的官能团耐受性以及采用环保型芳基硅烷等特点。通过克级合成和产物的进一步阐述,证明了这种方法的实用性。此外,Rh(III)催化的 C-H 活化被认为是反应机理中的关键步骤。

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