Published April 25, 2011
| Supplemental Material
Journal Article
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Functionalization of Rhenium Aryl Bonds by O-Atom Transfer
Abstract
Aryltrioxorhenium (ArReO_3) has been demonstrated to show rapid oxy-functionalization upon reaction with O-atom donors, YO, to selectively generate the corresponding phenols in near quantitative yields. (18)^O-Labeling experiments show that the oxygen in the products is exclusively from YO. DFT studies reveal a 10.7 kcal/mol barrier (Ar = Ph) for oxy-functionalization with H_2O_2 via a Baeyer-Villiger type mechanism involving nudeophilic attack of the aryl group on an electrophilic oxygen of YO coordinated to rhenium.
Additional Information
© 2011 American Chemical Society. Received March 17, 2011. Published March 29, 2011. The authors acknowledge the Chevron Corporation, the Center for Catalytic Hydrocarbon Functionalization, a DOE Energy Frontier Research Center (DOE DE-SC000-1298), and The Scripps Research Institute for financial support of this research.Attached Files
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Additional details
- Eprint ID
- 23540
- DOI
- 10.1021/om2002365
- Resolver ID
- CaltechAUTHORS:20110504-073755259
- Chevron Corporation
- DE-SC0001298
- Department of Energy (DOE)
- Scripps Research Institute
- Created
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2011-05-04Created from EPrint's datestamp field
- Updated
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2021-11-09Created from EPrint's last_modified field