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Title: Evidence of CuI/CuII Redox Process by X-ray Absorption and EPR Spectroscopy: Direct Synthesis of Dihydrofurans from b-Ketocarbonyl Derivatives and Olefins

Abstract: The CuI/CuII and CuI/CuIII catalytic cycles have been subject to intense debate in the field of copper-catalyzed oxidative coupling reactions. A mechanistic study on the CuI/CuII redox process, by X-ray absorption (XAS) and electron paramagnetic resonance (EPR) spectroscopies, has elucidated the reduction mechanism of CuII to CuI by 1,3-diketone and detailed investigation revealed that the halide ion is important for the reduction process. The oxidative nature of the thereby-formed CuI has also been studied by XAS and EPR spectroscopy. This mechanistic information is applicable to the copper-catalyzed oxidative cyclization of b-ketocarbonyl derivatives to dihydrofurans. This protocol provides an ideal route to highly substituted dihydrofuran rings from easily available 1,3-dicarbonyls and olefins. Copper
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Publication Date:
OSTI Identifier:
DOE Contract Number:
Resource Type:
Journal Article
Resource Relation:
Journal Name: Chemistry - A European Journal (Online); Journal Volume: 21; Journal Issue: 52
ChemPubSoc Europe
Research Org:
Argonne National Laboratory (ANL)
Sponsoring Org:
National Synchrotron Radiation Research Center (NSRRC); Ministry of Science and Technology of the People's Republic of China; Argonne National Laboratory - Chemical Sciences and Engineering Division; USDOE Office of Science - Office of Basic Energy Sciences; Materials Research Collaborative Access Team (MRCAT); National Natural Science Foundation of China (NSFC)
Country of Publication:
United States