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Functionalization of Rhenium Aryl Bonds by O-Atom Transfer

Bischof, Steven M. and Cheng, Mu-Jeng and Nielsen, Robert J. and Gunnoe, T. Brent and Goddard, William A., III and Periana, Roy A. (2011) Functionalization of Rhenium Aryl Bonds by O-Atom Transfer. Organometallics, 30 (8). pp. 2079-2082. ISSN 0276-7333. https://resolver.caltech.edu/CaltechAUTHORS:20110504-073755259

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/om2002365DOIArticle
http://pubs.acs.org/doi/abs/10.1021/om2002365PublisherArticle
ORCID:
AuthorORCID
Cheng, Mu-Jeng0000-0002-8121-0485
Nielsen, Robert J.0000-0002-7962-0186
Goddard, William A., III0000-0003-0097-5716
Periana, Roy A.0000-0001-7838-257X
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.
Funders:
Funding AgencyGrant Number
Chevron CorporationUNSPECIFIED
Department of Energy (DOE)DE-SC0001298
Scripps Research InstituteUNSPECIFIED
Issue or Number:8
Record Number:CaltechAUTHORS:20110504-073755259
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110504-073755259
Official Citation:Functionalization of Rhenium Aryl Bonds by O-Atom Transfer Steven M. Bischof, Mu-Jeng Cheng, Robert J. Nielsen, T. Brent Gunnoe, William A. Goddard III, Roy A. Periana Organometallics 2011 30 (8), 2079-2082
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:23540
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:04 May 2011 17:42
Last Modified:03 Oct 2019 02:47

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