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
- Research Organization:
- Argonne National Lab. (ANL), Argonne, IL (United States)
- Sponsoring Organization:
- 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 (SC), Basic Energy Sciences (BES); Materials Research Collaborative Access Team (MRCAT); National Natural Science Foundation of China (NNSFC)
- DOE Contract Number:
- AC02-06CH11357
- OSTI ID:
- 1241302
- Journal Information:
- Chemistry - A European Journal (Online), Vol. 21, Issue 52; ISSN 1521-3765
- Publisher:
- ChemPubSoc Europe
- Country of Publication:
- United States
- Language:
- English
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