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.

Org Lett 2017 05 19;19(9):2330-2333. Epub 2017 Apr 19.

College of Chemistry and Molecular Sciences, the Institute for Advanced Studies (IAS), Wuhan University , Wuhan, Hubei 430072, P.R. China.

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.

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http://dx.doi.org/10.1021/acs.orglett.7b00865DOI Listing
May 2017
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