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

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 n...

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Published inOrganic letters Vol. 19; no. 9; pp. 2330 - 2333
Main Authors Wu, Yong, Huang, Zhiyuan, Luo, Yi, Liu, Dong, Deng, Yi, Yi, Hong, Lee, Jyh-Fu, Pao, Chih-Wen, Chen, Jeng-Lung, Lei, Aiwen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.05.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
H FUNCTIONALIZATION
CROSS-COUPLING REACTIONS
MECHANISTIC INSIGHTS
CLICK CHEMISTRY
POLYSUBSTITUTED FURANS
TERMINAL ALKYNES
OXIDATIVE ANNULATION
METAL-HYDRIDES
RADICAL-ADDITION
EPR SPECTROSCOPY
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00865