Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin

Liu, W.; Huang, X.; Cheng, M. -J.; Nielsen, R. J.; Goddard, W. A.; Groves, J. T.

doi:10.1126/science.1222327

Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin

Journal Article · Thu Sep 13 04:00:00 EDT 2012 · Science

DOI:https://doi.org/10.1126/science.1222327· OSTI ID:1381275

Liu, W.; Huang, X.; Cheng, M. -J.; Nielsen, R. J.; Goddard, W. A.; Groves, J. T.

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Catalytic Hydrocarbon Functionalization (CCHF)

Sponsoring Organization:: USDOE SC Office of Basic Energy Sciences (SC-22)

DOE Contract Number:: SC0001298

OSTI ID:: 1381275

Journal Information:: Science, Journal Name: Science Journal Issue: 6100 Vol. 337; ISSN 0036-8075

Publisher:: AAAS

Country of Publication:: United States

Language:: English

References (38)

Fluorine Transfer to Alkyl Radicals Rueda-Becerril, Montserrat; Chatalova Sazepin, Claire; Leung, Joe C. T. Journal of the American Chemical Society, Vol. 134, Issue 9 https://doi.org/10.1021/ja211679v	journal	February 2012
A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging Lee, E.; Kamlet, A. S.; Powers, D. C. Science, Vol. 334, Issue 6056 https://doi.org/10.1126/science.1212625	journal	November 2011
Enantioselective Ring Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual-Catalyst System Kalow, Julia A.; Doyle, Abigail G. Journal of the American Chemical Society, Vol. 132, Issue 10 https://doi.org/10.1021/ja100161d	journal	March 2010
Fluorine in Pharmaceuticals: Looking Beyond Intuition Muller, K.; Faeh, C.; Diederich, F. Science, Vol. 317, Issue 5846 https://doi.org/10.1126/science.1131943	journal	September 2007
Silver-Catalyzed Decarboxylative Fluorination of Aliphatic Carboxylic Acids in Aqueous Solution Yin, Feng; Wang, Zhentao; Li, Zhaodong Journal of the American Chemical Society, Vol. 134, Issue 25 https://doi.org/10.1021/ja3048255	journal	June 2012
The Catalytic Pathway of Cytochrome P450cam at Atomic Resolution Schlichting, I. Science, Vol. 287, Issue 5458 https://doi.org/10.1126/science.287.5458.1615	journal	March 2000
Chemo-enzymatic fluorination of unactivated organic compounds Rentmeister, Andrea; Arnold, Frances H.; Fasan, Rudi Nature Chemical Biology, Vol. 5, Issue 1 https://doi.org/10.1038/nchembio.128	journal	November 2008
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Engineering Fluorometabolite Production: Fluorinase Expression in Salinispora tropica Yields Fluorosalinosporamide ^† Eustáquio, Alessandra S.; O’Hagan, David; Moore, Bradley S. Journal of Natural Products, Vol. 73, Issue 3 https://doi.org/10.1021/np900719u	journal	March 2010
Dissection of the Mechanism of Manganese Porphyrin-Catalyzed Chlorine Dioxide Generation Umile, Thomas P.; Wang, Dong; Groves, John T. Inorganic Chemistry, Vol. 50, Issue 20 https://doi.org/10.1021/ic201430v	journal	October 2011
Molecular Imaging with PET Ametamey, Simon M.; Honer, Michael; Schubiger, Pius August Chemical Reviews, Vol. 108, Issue 5 https://doi.org/10.1021/cr0782426	journal	May 2008
Synthesis, characterization, and reactivity of oxomanganese(IV) porphyrin complexes Groves, John T.; Stern, Michael K. Journal of the American Chemical Society, Vol. 110, Issue 26 https://doi.org/10.1021/ja00234a009	journal	December 1988
Reactive oxygen species have a causal role in multiple forms of insulin resistance Houstis, Nicholas; Rosen, Evan D.; Lander, Eric S. Nature, Vol. 440, Issue 7086 https://doi.org/10.1038/nature04634	journal	April 2006
Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21+G basis set for first-row elements, Li-F Clark, Timothy; Chandrasekhar, Jayaraman; Spitznagel, G�nther W. Journal of Computational Chemistry, Vol. 4, Issue 3 https://doi.org/10.1002/jcc.540040303	journal	October 1983
Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements Francl, Michelle M.; Pietro, William J.; Hehre, Warren J. The Journal of Chemical Physics, Vol. 77, Issue 7, p. 3654-3665 https://doi.org/10.1063/1.444267	journal	October 1982
Elemental fluorine in organic chemistry (1997–2006) Sandford, Graham Journal of Fluorine Chemistry, Vol. 128, Issue 2 https://doi.org/10.1016/j.jfluchem.2006.10.019	journal	February 2007
New Model for Calculation of Solvation Free Energies: Correction of Self-Consistent Reaction Field Continuum Dielectric Theory for Short-Range Hydrogen-Bonding Effects Marten, Bryan; Kim, Kyungsun; Cortis, Christian The Journal of Physical Chemistry, Vol. 100, Issue 28 https://doi.org/10.1021/jp953087x	journal	January 1996
Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions Krishnan, R.; Binkley, J. S.; Seeger, R. The Journal of Chemical Physics, Vol. 72, Issue 1 https://doi.org/10.1063/1.438955	journal	January 1980
A “Push−Pull” Mechanism for Heterolytic O−O Bond Cleavage in Hydroperoxo Manganese Porphyrins Jin, Ning; Lahaye, Dorothée E.; Groves, John T. Inorganic Chemistry, Vol. 49, Issue 24 https://doi.org/10.1021/ic1015274	journal	December 2010
Enzymatic functionalization of carbon–hydrogen bonds Lewis, Jared C.; Coelho, Pedro S.; Arnold, Frances H. Chem. Soc. Rev., Vol. 40, Issue 4 https://doi.org/10.1039/c0cs00067a	journal	January 2011
Correlation consistent valence basis sets for use with the Stuttgart–Dresden–Bonn relativistic effective core potentials: The atoms Ga–Kr and In–Xe Martin, Jan M. L.; Sundermann, Andreas The Journal of Chemical Physics, Vol. 114, Issue 8 https://doi.org/10.1063/1.1337864	journal	February 2001
Combined Effects on Selectivity in Fe-Catalyzed Methylene Oxidation Chen, M. S.; White, M. C. Science, Vol. 327, Issue 5965 https://doi.org/10.1126/science.1183602	journal	January 2010
Density-functional exchange-energy approximation with correct asymptotic behavior Becke, A. D. Physical Review A, Vol. 38, Issue 6 https://doi.org/10.1103/PhysRevA.38.3098	journal	September 1988
Substrate positioning controls the partition between halogenation and hydroxylation in the aliphatic halogenase, SyrB2 Matthews, M. L.; Neumann, C. S.; Miles, L. A. Proceedings of the National Academy of Sciences, Vol. 106, Issue 42 https://doi.org/10.1073/pnas.0909649106	journal	October 2009
High-valent iron in chemical and biological oxidations Groves, John T. Journal of Inorganic Biochemistry, Vol. 100, Issue 4 https://doi.org/10.1016/j.jinorgbio.2006.01.012	journal	April 2006
A new mixing of Hartree–Fock and local density‐functional theories Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 2 https://doi.org/10.1063/1.464304	journal	January 1993
Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides Watson, D. A.; Su, M.; Teverovskiy, G. Science, Vol. 325, Issue 5948 https://doi.org/10.1126/science.1178239	journal	August 2009
Safe and Convenient Procedure for Solvent Purification Pangborn, Amy B.; Giardello, Michael A.; Grubbs, Robert H. Organometallics, Vol. 15, Issue 5, p. 1518-1520 https://doi.org/10.1021/om9503712	journal	January 1996
Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules Hehre, W. J.; Ditchfield, R.; Pople, J. A. The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261 https://doi.org/10.1063/1.1677527	journal	March 1972
Trans-dioxo Manganese(V) Porphyrins Jin, Ning; Ibrahim, Mohammed; Spiro, Thomas G. Journal of the American Chemical Society, Vol. 129, Issue 41 https://doi.org/10.1021/ja0761737	journal	October 2007
Accurate First Principles Calculation of Molecular Charge Distributions and Solvation Energies from Ab Initio Quantum Mechanics and Continuum Dielectric Theory Tannor, David J.; Marten, Bryan; Murphy, Robert Journal of the American Chemical Society, Vol. 116, Issue 26 https://doi.org/10.1021/ja00105a030	journal	December 1994
Revisiting the Mechanism of P450 Enzymes with the Radical Clocks Norcarane and Spiro[2,5]octane Auclair, Karine; Hu, Zhengbo; Little, Dorothy M. Journal of the American Chemical Society, Vol. 124, Issue 21 https://doi.org/10.1021/ja025608h	journal	May 2002
Silver-Catalyzed Late-Stage Fluorination Tang, Pingping; Furuya, Takeru; Ritter, Tobias Journal of the American Chemical Society, Vol. 132, Issue 34 https://doi.org/10.1021/ja105834t	journal	September 2010
Catalysis for fluorination and trifluoromethylation Furuya, Takeru; Kamlet, Adam S.; Ritter, Tobias Nature, Vol. 473, Issue 7348 https://doi.org/10.1038/nature10108	journal	May 2011
Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals Hay, P. Jeffrey; Wadt, Willard R. The Journal of Chemical Physics, Vol. 82, Issue 1, p. 299-310 https://doi.org/10.1063/1.448975	journal	January 1985
If CH Bonds Could Talk: Selective CH Bond Oxidation Newhouse, Timothy; Baran, Phil S. Angewandte Chemie International Edition, Vol. 50, Issue 15 https://doi.org/10.1002/anie.201006368	journal	March 2011
Manganese Porphyrins Catalyze Selective C−H Bond Halogenations Liu, Wei; Groves, John T. Journal of the American Chemical Society, Vol. 132, Issue 37 https://doi.org/10.1021/ja105548x	journal	September 2010
Activating unreactive sites of organic molecules using elemental fluorine Rozen, Shlomo; Gal, Chava The Journal of Organic Chemistry, Vol. 52, Issue 13 https://doi.org/10.1021/jo00389a024	journal	June 1987

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