Herrera Fernando, Luna Amparo, Almendros Pedro
Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain.
Instituto de Química Orgánica General, IQOG, CSIC, Juan de la Cierva 3, 28006-Madrid, Spain.
Org Lett. 2020 Dec 18;22(24):9490-9494. doi: 10.1021/acs.orglett.0c03482. Epub 2020 Nov 24.
The first coupling of α-allenols, sulfur dioxide, and arenediazonium salts is presented. The three-component reaction which is promoted by visible light can be easily accomplished using DABSO as a sulfur dioxide surrogate in the presence of a photoredox catalyst. In this manner, a broad range of electron-rich and electron-deficient aryl substituents are well accommodated in the sulfonylation-rearrangement cascade to afford the 2,2-disubstituted 3-(arylsulfonyl)but-3-enals in reasonable yields. Based on control experiments, a radical mechanism which does imply 1,2-aryl migration has been proposed.
首次报道了α-联烯醇、二氧化硫和芳基重氮盐的偶联反应。在光氧化还原催化剂存在下，以DABSO作为二氧化硫替代物，可见光促进的三组分反应能够轻松实现。通过这种方式，在磺酰化-重排串联反应中，各种富电子和缺电子的芳基取代基都能很好地兼容，以合理的产率得到2,2-二取代的3-(芳基磺酰基)丁-3-烯醛。基于对照实验，提出了一种确实涉及1,2-芳基迁移的自由基机理。
