CaltechAUTHORS
Published April 25, 2011 | Version Supplemental Material
Journal Article Open

Functionalization of Rhenium Aryl Bonds by O-Atom Transfer

Creators

  • 1. ROR icon Scripps Research Institute
  • 2. ROR icon California Institute of Technology
  • 3. ROR icon University of Virginia

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.

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Additional details

Identifiers

Eprint ID
23540
DOI
10.1021/om2002365
Resolver ID
CaltechAUTHORS:20110504-073755259

Related works

Describes
10.1021/om2002365 (DOI)

Funding

Chevron Corporation
Department of Energy (DOE)
DE-SC0001298
Scripps Research Institute

Dates

Created
2011-05-04
Created from EPrint's datestamp field
Updated
2021-11-09
Created from EPrint's last_modified field