Organic Letters
Organic Letters
5 years ago

X-ray Absorption and Electron Paramagnetic Resonance Guided Discovery of the Cu-Catalyzed Synthesis of Multiaryl-Substituted Furans from Aryl Styrene and Ketones Using DMSO as the Oxidant

X-ray Absorption and Electron Paramagnetic Resonance Guided Discovery of the Cu-Catalyzed Synthesis of Multiaryl-Substituted Furans from Aryl Styrene and Ketones Using DMSO as the Oxidant
Chih-Wen Pao, Hong Yi, Jyh-Fu Lee, Jeng-Lung Chen, Zhiyuan Huang, Aiwen Lei, Yi Luo, Dong Liu, Yong Wu, Yi Deng
The first example of DMSO serving not only as a solvent but also as an oxidant to promote the oxidation of Cu(I) to Cu(II) has been demonstrated. X-ray absorption and electron paramagnetic resonance evidence revealed a single-electron redox process where DMSO could oxidize Cu(I) to Cu(II). The novel discovery guided the rational design of copper-catalyzed oxidative cyclization of aryl ketones with styrenes to furans, providing a new method for the synthesis of multiaryl-substituted furans from cheap and readily available starting materials.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00865

DOI: 10.1021/acs.orglett.7b00865

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