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ICl/AgNO 共催化二芳基和芳基烷基炔烃的自由基氧化反应生成 1,2-二酮。

ICl/AgNO Co-Catalyzed Radical Oxidation of Diaryl- and Alkylarylalkynes into 1,2-Diketones.

机构信息

Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment , South China Normal University , Guangzhou 510006 , People's Republic of China.

Department of Chemistry and Biochemistry , Queens College of the City University of New York , 65-30 Kissena Blvd. , Queens , New York 11367 , United States.

出版信息

J Org Chem. 2019 Sep 6;84(17):11080-11090. doi: 10.1021/acs.joc.9b01667. Epub 2019 Aug 12.

Abstract

A novel ICl/AgNO co-catalyzed radical oxidation of diaryl- and alkylarylalkynes into 1,2-diketones is reported. The reaction proceeded smoothly under mild conditions and generated 1,2-diketones in moderate to good yields with a good tolerance of functional groups. Furthermore, the obtained C4-(1,2-diketoaryl)isoxazoles could react smoothly with 1,2-diaminobenzene to form C4-(3-arylquinoxalin-2-yl)isoxazoles. At last, a new one-pot strategy for the synthesis of quinoxalines from 1,2-diphenylethynes and 1,2-diaminobenzene is also reported.

摘要

一种新型的 ICl/AgNO 共催化的芳基和烷基芳基炔烃的自由基氧化反应,生成 1,2-二酮。该反应在温和的条件下顺利进行,具有良好的官能团耐受性,中等至良好的产率得到 1,2-二酮。此外,得到的 C4-(1,2-二酮芳基)异恶唑可以与 1,2-二氨基苯顺利反应,形成 C4-(3-芳基喹喔啉-2-基)异恶唑。最后,还报道了一种从 1,2-二苯乙炔和 1,2-二氨基苯一锅法合成喹喔啉的新策略。

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