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Experimental Demonstration and Density Functional Theory Mechanistic Analysis of Arene C–H Bond Oxidation and Product Protection by Osmium Tetroxide in a Strongly Basic/Nucleophilic Solvent

Journal Article · · Journal of Organic Chemistry
 [1];  [2];  [3];  [2]
  1. The Scripps Energy and Materials Center, Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, United States; OSTI
  2. Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States
  3. The Scripps Energy and Materials Center, Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, United States

Not provided.

Research Organization:
Brigham Young Univ., Provo, UT (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
DOE Contract Number:
SC0018329
OSTI ID:
2420765
Journal Information:
Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 21 Vol. 87; ISSN 0022-3263
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English

References (25)

Divergence between Organometallic and Single-Electron-Transfer Mechanisms in Copper(II)-Mediated Aerobic C–H Oxidation journal June 2013
Density Functional Study of the [2+2]- and [2+3]-Cycloaddition Mechanisms for the Osmium-Catalyzed Dihydroxylation of Olefins journal January 1997
Theory Does Not Support an Osmaoxetane Intermediate in the Osmium-Catalyzed Dihydroxylation of Olefins journal January 1996
Cu(II)-Catalyzed Functionalizations of Aryl C−H Bonds Using O 2 as an Oxidant journal May 2006
Designing Catalysts for Functionalization of Unactivated C–H Bonds Based on the CH Activation Reaction journal January 2012
Quantum Mechanical Continuum Solvation Models journal August 2005
Copper-Mediated Hydroxylation of Arenes and Heteroarenes Directed by a Removable Bidentate Auxiliary journal July 2014
Identification of monodentate oxazoline as a ligand for copper-promoted ortho-C–H hydroxylation and amination journal January 2017
Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers journal January 2016
Diradical versus Concerted Mechanisms for the Dihydroxylation of Protoanemonin by OsO4 and OsO4−NH3 − The Effect of the Base in the Reaction journal February 2003
Industrial catalytic processes—phenol production journal February 2005
Oxidation of Tertiary Silanes by Osmium Tetroxide journal May 2007
Cu(II)-Mediated C(sp2)–H Hydroxylation journal August 2015
Alkane Oxidation by Osmium Tetroxide journal March 2005
Cu-Catalyzed Mild C(sp2)–H Functionalization Assisted by Carboxylic Acids en Route to Hydroxylated Arenes journal June 2013
Ligand-Assisted Reduction of Osmium Tetroxide with Molecular Hydrogen via a [3+2] Mechanism journal February 2005
Acceleration of Nucleophilic CH Activation by Strongly Basic Solvents journal September 2010
A DFT study to unravel the ligand exchange kinetics and thermodynamics of OsVIIIoxo/hydroxido/aqua complexes in aqueous matrices journal January 2016
Copper(II)-Catalyzed Ortho-Acyloxylation of the 2-Arylpyridines sp2 C−H Bonds with Anhydrides, Using O2 as Terminal Oxidant journal March 2010
Controlling Site Selectivity in Palladium-Catalyzed C–H Bond Functionalization journal January 2012
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals journal July 2007
A tautomeric ligand enables directed C‒H hydroxylation with molecular oxygen journal June 2021
Pd(II) catalyzed acetoxylation of arenes with iodosyl acetate journal April 1996
Experimental and Theoretical Kinetic Isotope Effects for Asymmetric Dihydroxylation. Evidence Supporting a Rate-Limiting “(3 + 2)” Cycloaddition journal October 1997
Distortion, Interaction, and Conceptual DFT Perspectives of MO 4 −Alkene (M = Os, Re, Tc, Mn) Cycloadditions journal February 2009

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