Activation of carbon–hydrogen bonds and dihydrogen by 1,2-CH-addition across metal–heteroatom bonds

Webb, Joanna R.; Burgess, Samantha A.; Cundari, Thomas R.; Gunnoe, T. Brent

doi:10.1039/c3dt52164h

Title: Activation of carbon–hydrogen bonds and dihydrogen by 1,2-CH-addition across metal–heteroatom bonds

Journal Article · Tue Jan 01 00:00:00 EST 2013 · Dalton Transactions

DOI:https://doi.org/10.1039/c3dt52164h· OSTI ID:1382880

Webb, Joanna R.; Burgess, Samantha A.; Cundari, Thomas R.; Gunnoe, T. Brent

Cite

Export

Save

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: SC0001298

OSTI ID:: 1382880

Journal Information:: Dalton Transactions, Vol. 42, Issue 48; Related Information: CCHF partners with University of Virginia (lead); Brigham Young University; California Institute of Technology; Colorado School of Mines; University of Maryland; University of North Carolina, Chapel Hill; University of North Texas; Princeton University; The Scripps Research Institute; Yale University; ISSN 1477-9226

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

References (113)

Designing Catalysts for Functionalization of Unactivated C–H Bonds Based on the CH Activation Reaction Hashiguchi, Brian G.; Bischof, Steven M.; Konnick, Michael M. Accounts of Chemical Research, Vol. 45, Issue 6 https://doi.org/10.1021/ar200250r	journal	January 2012
Phenyl-to-Oxo Migration in an Electrophilic Rhenium(VII) Dioxo Complex Brown, Seth N.; Mayer, James M. Journal of the American Chemical Society, Vol. 118, Issue 48 https://doi.org/10.1021/ja962087n	journal	January 1996
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
Nonheme Iron-Mediated Amination of C(sp ³ )–H Bonds. Quinquepyridine-Supported Iron-Imide/Nitrene Intermediates by Experimental Studies and DFT Calculations Liu, Yungen; Guan, Xiangguo; Wong, Ella Lai-Ming Journal of the American Chemical Society, Vol. 135, Issue 19 https://doi.org/10.1021/ja3122526	journal	May 2013
Pt(II) and Pt(IV) Amido, Aryloxide, and Hydrocarbyl Complexes: Synthesis, Characterization, and Reaction with Dihydrogen and Substrates that Possess C−H Bonds Webb, Joanna R.; Munro-Leighton, Colleen; Pierpont, Aaron W. Inorganic Chemistry, Vol. 50, Issue 9 https://doi.org/10.1021/ic200153n	journal	March 2011
Ru-, Rh-, and Pd-Catalyzed C−C Bond Formation Involving C−H Activation and Addition on Unsaturated Substrates: Reactions and Mechanistic Aspects Ritleng, Vincent; Sirlin, Claude; Pfeffer, Michel Chemical Reviews, Vol. 102, Issue 5 https://doi.org/10.1021/cr0104330	journal	May 2002
Synthesis and Reactivity of the Octahedral d ⁶ Parent Amido Complexes TpRu(L)(L‘)(NH ₂ ) (Tp = Hydridotris(pyrazolyl)borate; L = L‘ = PMe ₃ , P(OMe) ₃ ; L = CO, L‘ = PPh ₃ ) and [TpRu(PPh ₃ )(NH ₂ ) ₂ ][Li] Jayaprakash, K. N.; Conner, David; Gunnoe, T. Brent Organometallics, Vol. 20, Issue 25 https://doi.org/10.1021/om010739x	journal	December 2001
Synthesis of a First-Row Transition Metal Parent Amido Complex and Carbon Monoxide Insertion into the Amide N−H Bond Fox, Daniel J.; Bergman, Robert G. Journal of the American Chemical Society, Vol. 125, Issue 30 https://doi.org/10.1021/ja035707a	journal	July 2003
Inter- and Intramolecular Experimental and Calculated Equilibrium Isotope Effects for (silox) ₂ ( ^t Bu ₃ SiND)TiR + RH (silox = ^t Bu ₃ SiO): Inferred Kinetic Isotope Effects for RH/D Addition to Transient (silox) ₂ TiNSi ^t Bu ₃ Slaughter, LeGrande M.; Wolczanski, Peter T.; Klinckman, Thomas R. Journal of the American Chemical Society, Vol. 122, Issue 33 https://doi.org/10.1021/ja000112q	journal	August 2000
Oxygen-Atom Transfer from Nitrous Oxide to an Organonickel(II) Phosphine Complex. Syntheses and Reactions of New Nickel(II) Aryloxides and the Crystal Structure of [cyclic] (Me2PCH2CH2PMe2)Ni(O-o-C6H4CMe2CH2) Koo, Kwangmo; Hillhouse, Gregory L.; Rheingold, Arnold L. Organometallics, Vol. 14, Issue 1 https://doi.org/10.1021/om00001a062	journal	January 1995
Selective Intermolecular Carbon-Hydrogen Bond Activation by Synthetic Metal Complexes in Homogeneous Solution Arndtsen, Bruce A.; Bergman, Robert G.; Mobley, T. Andrew Accounts of Chemical Research, Vol. 28, Issue 3 https://doi.org/10.1021/ar00051a009	journal	March 1995
Complex N-Heterocycle Synthesis via Iron-Catalyzed, Direct C-H Bond Amination Hennessy, E. T.; Betley, T. A. Science, Vol. 340, Issue 6132 https://doi.org/10.1126/science.1233701	journal	May 2013
Computational Study of the Mechanism of Cyclometalation by Palladium Acetate Davies, David L.; Donald, Steven M. A.; Macgregor, Stuart A. Journal of the American Chemical Society, Vol. 127, Issue 40 https://doi.org/10.1021/ja052047w	journal	October 2005
Cyclohexane and Benzene Amination by Catalytic Nitrene Insertion into C−H Bonds with the Copper-Homoscorpionate Catalyst Tp ^Br3 Cu(NCMe) Díaz-Requejo, M. Mar; Belderraín, Tomás R.; Nicasio, M. Carmen Journal of the American Chemical Society, Vol. 125, Issue 40 https://doi.org/10.1021/ja037072l	journal	October 2003
A Comprehensive Investigation of the Chemistry and Basicity of a Parent Amidoruthenium Complex Fulton, J. Robin; Sklenak, Stepan; Bouwkamp, Marco W. Journal of the American Chemical Society, Vol. 124, Issue 17 https://doi.org/10.1021/ja011876o	journal	April 2002
Mechanistic Analysis of Hydroarylation Catalysts Oxgaard, Jonas; Periana, Roy A.; Goddard, William A. Journal of the American Chemical Society, Vol. 126, Issue 37 https://doi.org/10.1021/ja048841j	journal	September 2004
Influence of Filled dπ-Manifold and L/L‘ Ligands on the Structure, Basicity, and Bond Rotations of the Octahedral and d ⁶ Amido Complexes TpRu(L)(L‘)(NHPh) (Tp = Hydridotris(pyrazolyl)borate; L = L‘ = PMe ₃ or P(OMe) ₃ , or L = CO and L‘ = PPh ₃ ): Solid-State Structures of [TpRu(PMe ₃ ) ₂ (NH ₂ Ph)][OTf], [TpRu{P(OMe) ₃ } ₂ (NH ₂ Ph)][OTf], and TpRu{P(OMe) ₃ } ₂ (NHPh) Conner, David; Jayaprakash, K. N.; Gunnoe, T. Brent Inorganic Chemistry, Vol. 41, Issue 11 https://doi.org/10.1021/ic020163j	journal	June 2002
Carbon−Hydrogen Bond Activation by Titanium Imido Complexes. Computational Evidence for the Role of Alkane Adducts in Selective C−H Activation Cundari, Thomas R.; Klinckman, Thomas R.; Wolczanski, Peter T. Journal of the American Chemical Society, Vol. 124, Issue 7 https://doi.org/10.1021/ja016248l	journal	February 2002
Electrophilic, Ambiphilic, and Nucleophilic C−H Bond Activation: Understanding the Electronic Continuum of C−H Bond Activation Through Transition-State and Reaction Pathway Interaction Energy Decompositions Ess, Daniel H.; Goddard, William A.; Periana, Roy A. Organometallics, Vol. 29, Issue 23 https://doi.org/10.1021/om100879y	journal	December 2010
Alkane C–H activation and functionalization with homogeneous transition metal catalysts: a century of progress—a new millennium in prospect Crabtree, Robert H. Journal of the Chemical Society, Dalton Transactions, Issue 17 https://doi.org/10.1039/b103147n	journal	January 2001
Synthesis of an Iron Parent Amido Complex and a Comparison of Its Reactivity with the Ruthenium Analog Fox, Daniel J.; Bergman, Robert G. Organometallics, Vol. 23, Issue 8 https://doi.org/10.1021/om0499660	journal	April 2004
Metalloradical activation of methane Sherry, Alan E.; Wayland, Bradford B. Journal of the American Chemical Society, Vol. 112, Issue 3 https://doi.org/10.1021/ja00159a064	journal	January 1990
Comparative reactivities of hydrocarbon carbon-hydrogen bonds with a transition-metal complex Jones, William D.; Feher, Frank J. Accounts of Chemical Research, Vol. 22, Issue 3 https://doi.org/10.1021/ar00159a002	journal	March 1989
A Terminal Ni(III)−Imide with Diverse Reactivity Pathways Kogut, Elzbieta; Wiencko, Heather L.; Zhang, Libei Journal of the American Chemical Society, Vol. 127, Issue 32 https://doi.org/10.1021/ja0533186	journal	August 2005
Transition metal imido complexes Cundari, Thomas R. Journal of the American Chemical Society, Vol. 114, Issue 20 https://doi.org/10.1021/ja00046a037	journal	September 1992
Methane: a new frontier in organometallic chemistry Cavaliere, Vincent N.; Mindiola, Daniel J. Chemical Science, Vol. 3, Issue 12 https://doi.org/10.1039/c2sc20530k	journal	January 2012
Generation, alkyne cycloaddition, arene carbon-hydrogen activation, nitrogen-hydrogen activation and dative ligand trapping reactions of the first monomeric imidozirconocene (Cp2Zr:NR) complexes Walsh, Patrick J.; Hollander, Frederick J.; Bergman, Robert G. Journal of the American Chemical Society, Vol. 110, Issue 26 https://doi.org/10.1021/ja00234a043	journal	December 1988
Methane and benzene activation via transient (tert-Bu3SiNH)2Zr:NSi-tert-Bu3 Cummins, Christopher C.; Baxter, Steven M.; Wolczanski, Peter T. Journal of the American Chemical Society, Vol. 110, Issue 26 https://doi.org/10.1021/ja00234a044	journal	December 1988
Hydrogen-hydrogen and carbon-hydrogen activation reactions at d0 metal centers Rabaa, H.; Saillard, J. Y.; Hoffmann, R. Journal of the American Chemical Society, Vol. 108, Issue 15 https://doi.org/10.1021/ja00275a015	journal	July 1986
Activation of Carbon−Hydrogen Bonds via 1,2-Addition across M−X (X = OH or NH ₂ ) Bonds of d ⁶ Transition Metals as a Potential Key Step in Hydrocarbon Functionalization: A Computational Study Cundari, Thomas R.; Grimes, Thomas V.; Gunnoe, T. Brent Journal of the American Chemical Society, Vol. 129, Issue 43 https://doi.org/10.1021/ja074125g	journal	October 2007
Methane activation and exchange by titanium-carbon multiple bonds Flores, Jaime A.; Cavaliere, Vincent N.; Buck, Dominik Chemical Science, Vol. 2, Issue 8 https://doi.org/10.1039/c1sc00138h	journal	January 2011
Carboxylate-Assisted Transition-Metal-Catalyzed C−H Bond Functionalizations: Mechanism and Scope Ackermann, Lutz Chemical Reviews, Vol. 111, Issue 3 https://doi.org/10.1021/cr100412j	journal	March 2011
Co(III) Imidos Exhibiting Spin Crossover and C–H Bond Activation King, Evan R.; Sazama, Graham T.; Betley, Theodore A. Journal of the American Chemical Society, Vol. 134, Issue 43 https://doi.org/10.1021/ja307699u	journal	October 2012
Hydrogenolysis of Palladium(II) Hydroxide and Methoxide Pincer Complexes Fulmer, Gregory R.; Muller, Richard P.; Kemp, Richard A. Journal of the American Chemical Society, Vol. 131, Issue 4 https://doi.org/10.1021/ja807936q	journal	February 2009
Evidence for the Existence of Terminal Scandium Imidos: Mechanistic Studies Involving Imido–Scandium Bond Formation and C–H Activation Reactions Wicker, Benjamin F.; Fan, Hongjun; Hickey, Anne K. Journal of the American Chemical Society, Vol. 134, Issue 49 https://doi.org/10.1021/ja307279r	journal	November 2012
Hydrogen−Deuterium Exchange between TpRu(PMe ₃ )(L)X (L = PMe ₃ and X = OH, OPh, Me, Ph, or NHPh; L = NCMe and X = Ph) and Deuterated Arene Solvents: Evidence for Metal-Mediated Processes Feng, Yuee; Lail, Marty; Foley, Nicholas A. Journal of the American Chemical Society, Vol. 128, Issue 24 https://doi.org/10.1021/ja0615775	journal	June 2006
Methane Activation by Group VB Bis(imido) Complexes Cundari, Thomas R. Organometallics, Vol. 13, Issue 8 https://doi.org/10.1021/om00020a014	journal	August 1994
Copper-Nitrene Complexes in Catalytic CH Amination Badiei, Yosra M.; Dinescu, Adriana; Dai, Xuliang Angewandte Chemie International Edition, Vol. 47, Issue 51 https://doi.org/10.1002/anie.200804304	journal	December 2008
Mechanistic Studies on the Hydroxylation of Methane by Methane Monooxygenase Baik, Mu-Hyun; Newcomb, Martin; Friesner, Richard A. Chemical Reviews, Vol. 103, Issue 6 https://doi.org/10.1021/cr950244f	journal	June 2003
C−H Bond Activation by a Ferric Methoxide Complex: A Model for the Rate-Determining Step in the Mechanism of Lipoxygenase Jonas, Robert T.; Stack, T. D. P. Journal of the American Chemical Society, Vol. 119, Issue 36 https://doi.org/10.1021/ja971503g	journal	September 1997
Hydrogen Bond Control of Dimensionality in Organometallic {2,6-Bis[(di- t -butylphosphino)methyl]phenyl}palladium(II) Compounds: Dimers, Chains, and a 3D-Net with an Apparent Channel Structure Johansson, Roger; Öhrström, Lars; Wendt, Ola F. Crystal Growth & Design, Vol. 7, Issue 10 https://doi.org/10.1021/cg060913q	journal	October 2007
CH Activation with an O-Donor Iridium−Methoxo Complex Tenn, William J.; Young, Kenneth J. H.; Bhalla, Gaurav Journal of the American Chemical Society, Vol. 127, Issue 41 https://doi.org/10.1021/ja051497l	journal	October 2005
A group theoretical analysis on transition-metal complexes with metal-ligand multiple bonds Lin, Zhenyang; Hall, Michael B. Coordination Chemistry Reviews, Vol. 123, Issue 1-2 https://doi.org/10.1016/0010-8545(93)85054-8	journal	February 1993
Carbon−Hydrogen Bond Activation: Two, Three, or More Mechanisms? Vastine, Benjamin Alan; Hall, Michael B. Journal of the American Chemical Society, Vol. 129, Issue 40 https://doi.org/10.1021/ja074518f	journal	September 2007
Perspectives on some challenges and approaches for developing the next generation of selective, low temperature, oxidation catalysts for alkane hydroxylation based on the CH activation reaction Periana, Roy A.; Bhalla, Gaurav; Tenn, William J. Journal of Molecular Catalysis A: Chemical, Vol. 220, Issue 1 https://doi.org/10.1016/j.molcata.2004.05.036	journal	September 2004
Terminal Amido and Imido Complexes of Three-Coordinate Nickel Mindiola, Daniel J.; Hillhouse, Gregory L. Journal of the American Chemical Society, Vol. 123, Issue 19 https://doi.org/10.1021/ja010358a	journal	May 2001
C−H Bond Activation of Hydrocarbons by an Imidozirconocene Complex Hoyt, Helen M.; Michael, Forrest E.; Bergman, Robert G. Journal of the American Chemical Society, Vol. 126, Issue 4 https://doi.org/10.1021/ja0385944	journal	January 2004
Mechanism of Palladium−Carbon Bond Oxidation: Dramatic Solvent Effect Kamaraj, Kaliappan; Bandyopadhyay, Debkumar Organometallics, Vol. 18, Issue 3 https://doi.org/10.1021/om980731w	journal	February 1999
Non-redox Oxy-Insertion via Organometallic Baeyer–Villiger Transformations: A Computational Hammett Study of Platinum(II) Complexes Figg, Travis M.; Cundari, Thomas R.; Gunnoe, T. Brent Organometallics, Vol. 30, Issue 14 https://doi.org/10.1021/om200258d	journal	July 2011
Activation of a C−H Bond in Indene by [(COD)Rh(μ ₂ -OH)] ₂ ^† Bercaw, John E.; Hazari, Nilay; Labinger, Jay A. Organometallics, Vol. 28, Issue 18 https://doi.org/10.1021/om9004498	journal	September 2009
Ru(II) Catalysts Supported by Hydridotris(pyrazolyl)borate for the Hydroarylation of Olefins: Reaction Scope, Mechanistic Studies, and Guides for the Development of Improved Catalysts Foley, Nicholas A.; Lee, John P.; Ke, Zhuofeng Accounts of Chemical Research, Vol. 42, Issue 5 https://doi.org/10.1021/ar800183j	journal	May 2009
Understanding and exploiting C–H bond activation Labinger, Jay A.; Bercaw, John E. Nature, Vol. 417, Issue 6888 https://doi.org/10.1038/417507a	journal	May 2002
Evidence for the Net Addition of Arene C−H Bonds across a Ru(II)−Hydroxide Bond Feng, Yuee; Lail, Marty; Barakat, Khaldoon A. Journal of the American Chemical Society, Vol. 127, Issue 41 https://doi.org/10.1021/ja054101e	journal	October 2005
Carbon–Oxygen Bond Formation via Organometallic Baeyer–Villiger Transformations: A Computational Study on the Impact of Metal Identity Figg, Travis M.; Webb, Joanna R.; Cundari, Thomas R. Journal of the American Chemical Society, Vol. 134, Issue 4 https://doi.org/10.1021/ja2102778	journal	January 2012
Design and study of homogeneous catalysts for the selective, low temperature oxidation of hydrocarbons Conley, Brian L.; Tenn, William J.; Young, Kenneth J. H. Journal of Molecular Catalysis A: Chemical, Vol. 251, Issue 1-2 https://doi.org/10.1016/j.molcata.2006.02.035	journal	May 2006
Functionalization of Rhenium Aryl Bonds by O-Atom Transfer Bischof, Steven M.; Cheng, Mu-Jeng; Nielsen, Robert J. Organometallics, Vol. 30, Issue 8 https://doi.org/10.1021/om2002365	journal	April 2011
A Predictably Selective Aliphatic C H Oxidation Reaction for Complex Molecule Synthesis Chen, M. S.; White, M. C. Science, Vol. 318, Issue 5851 https://doi.org/10.1126/science.1148597	journal	November 2007
Facile Functionalization of a Metal Carbon Bond by O-Atom Transfer Conley, Brian L.; Ganesh, Somesh K.; Gonzales, Jason M. Journal of the American Chemical Society, Vol. 128, Issue 28 https://doi.org/10.1021/ja062417w	journal	July 2006
Selectivities in Hydrocarbon Activation: Kinetic and Thermodynamic Investigations of Reversible 1,2-RH-Elimination from (silox) ₂ ( ^t Bu ₃ SiNH)TiR (silox = ^t Bu ₃ SiO) Bennett, Jordan L.; Wolczanski, Peter T. Journal of the American Chemical Society, Vol. 119, Issue 44 https://doi.org/10.1021/ja9707419	journal	November 1997
Activation of C−H Bonds by Metal Complexes Shilov, Alexander E.; Shul'pin, Georgiy B. Chemical Reviews, Vol. 97, Issue 8 https://doi.org/10.1021/cr9411886	journal	December 1997
Tris(phenylimido) complexes of tungsten: preparation and properties of the d0 W(:NR)3 functional group Chao, Yuan Wei; Rodgers, Paula M.; Wigley, David E. Journal of the American Chemical Society, Vol. 113, Issue 16 https://doi.org/10.1021/ja00016a090	journal	July 1991
Mechanistic Aspects of C−H Activation by Pt Complexes Lersch, Martin; Tilset, Mats Chemical Reviews, Vol. 105, Issue 6 https://doi.org/10.1021/cr030710y	journal	June 2005
Formation, Reactivity, and Properties of Nondative Late Transition Metal−Oxygen and −Nitrogen Bonds Fulton, J. Robin; Holland, Andrew W.; Fox, Daniel J. Accounts of Chemical Research, Vol. 35, Issue 1 https://doi.org/10.1021/ar000132x	journal	January 2002
Tri-tert-butylsilyl)imido complexes of titanium: benzene carbon-hydrogen activation and structure of [(tert-Bu3SiNH)Ti]2(.mu.-NSi-tert-Bu3)2 Cummins, Christopher C.; Schaller, Christopher P.; Van Duyne, Gregory D. Journal of the American Chemical Society, Vol. 113, Issue 8 https://doi.org/10.1021/ja00008a029	journal	April 1991
Aspects of Methane Chemistry Crabtree, Robert H. Chemical Reviews, Vol. 95, Issue 4 https://doi.org/10.1021/cr00036a005	journal	June 1995
Why Are There No Terminal Oxo Complexes of the Late Transition Metals? or The Importance of Metal–Ligand π Antibonding Interactions Mayer, James M. Comments on Inorganic Chemistry, Vol. 8, Issue 4 https://doi.org/10.1080/02603598808035790	journal	December 1988
Hydrocarbon Activation via Reversible 1,2-RH-Elimination from ( ^t Bu ₃ SiNH) ₃ ZrR: Synthetic, Structural, and Mechanistic Investigations Schaller, Christopher P.; Cummins, Christopher C.; Wolczanski, Peter T. Journal of the American Chemical Society, Vol. 118, Issue 3 https://doi.org/10.1021/ja950745i	journal	January 1996
C−H Bond Activation by a Ferric Methoxide Complex: Modeling the Rate-Determining Step in the Mechanism of Lipoxygenase Goldsmith, Christian R.; Jonas, Robert T.; Stack, T. Daniel P. Journal of the American Chemical Society, Vol. 124, Issue 1 https://doi.org/10.1021/ja016451g	journal	January 2002
Oxygenation of cyclopalladated N,N-dimethylbenzylamine complexes by inorganic and organic peroxides: oxygen insertion into the palladium-carbon bond Alsters, Paul L.; Teunissen, Herman T.; Boersma, Jaap Organometallics, Vol. 12, Issue 11 https://doi.org/10.1021/om00035a068	journal	November 1993
Theoretical study of the structures of electron-deficient d6 ML5 complexes. Importance of a .pi.-donating ligand Riehl, Jean Frederic; Jean, Yves; Eisenstein, Odile Organometallics, Vol. 11, Issue 2 https://doi.org/10.1021/om00038a035	journal	February 1992
Hydrogenolysis of Palladium(II) Hydroxide, Phenoxide, and Alkoxide Complexes Fulmer, Gregory R.; Herndon, Alexandra N.; Kaminsky, Werner Journal of the American Chemical Society, Vol. 133, Issue 44 https://doi.org/10.1021/ja205824q	journal	November 2011
Intermolecular Copper-Catalyzed Carbon−Hydrogen Bond Activation via Carbene Insertion Díaz-Requejo, M. Mar; Belderraín, Tomás R.; Nicasio, M. Carmen Journal of the American Chemical Society, Vol. 124, Issue 6 https://doi.org/10.1021/ja016798j	journal	February 2002
The σ-CAM Mechanism: σ Complexes as the Basis of σ-Bond Metathesis at Late-Transition-Metal Centers Perutz, Robin N.; Sabo-Etienne, Sylviane Angewandte Chemie International Edition, Vol. 46, Issue 15 https://doi.org/10.1002/anie.200603224	journal	April 2007
Mechanistic Analysis of Iridium Heteroatom C−H Activation: Evidence for an Internal Electrophilic Substitution Mechanism Oxgaard, Jonas; Tenn, William J.; Nielsen, Robert J. Organometallics, Vol. 26, Issue 7 https://doi.org/10.1021/om061189b	journal	March 2007
C–H Activation of Terminal Alkynes by Tris-(3,5-dimethylpyrazolyl)boraterhodiumneopentylisocyanide: New Metal–Carbon Bond Strengths Choi, Gyeongshin; Morris, James; Brennessel, William W. Journal of the American Chemical Society, Vol. 134, Issue 22 https://doi.org/10.1021/ja301095r	journal	May 2012
.sigma.-Bond metathesis for carbon-hydrogen bonds of hydrocarbons and Sc-R (R = H, alkyl, aryl) bonds of permethylscandocene derivatives. Evidence for noninvolvement of the .pi. system in electrophilic activation of aromatic and vinylic C-H bonds Thompson, Mark E.; Baxter, Steven M.; Bulls, A. Ray Journal of the American Chemical Society, Vol. 109, Issue 1 https://doi.org/10.1021/ja00235a031	journal	January 1987
Catalytic Oxy-Functionalization of Methane and Other Hydrocarbons: Fundamental Advancements and New Strategies Webb, Joanna R.; Bolaño, Tamara; Gunnoe, T. Brent ChemSusChem, Vol. 4, Issue 1 https://doi.org/10.1002/cssc.201000319	journal	December 2010
Catalytic Carbene Insertion into C−H Bonds Doyle, Michael P.; Duffy, Richard; Ratnikov, Maxim Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900239n	journal	February 2010
Octahedral Ru(II) Amido Complexes TpRu(L)(L‘)(NHR) (Tp = Hydridotris(pyrazolyl)borate; L = L‘ = P(OMe) ₃ or PMe ₃ or L = CO and L‘ = PPh ₃ ; R = H, Ph, or ^t Bu): Synthesis, Characterization, and Reactions with Weakly Acidic C−H Bonds Conner, David; Jayaprakash, K. N.; Wells, Michael B. Inorganic Chemistry, Vol. 42, Issue 15 https://doi.org/10.1021/ic034410a	journal	June 2003
Ligand Lone-Pair Influence on Hydrocarbon C−H Activation: A Computational Perspective ^△ Ess, Daniel H.; Gunnoe, T. Brent; Cundari, Thomas R. Organometallics, Vol. 29, Issue 24 https://doi.org/10.1021/om100974q	journal	December 2010
Elimination and Activation of Methane and Larger Hydrocarbons Cundari, Thomas R.; Matsunaga, Nikita; Moody, Eddie W. The Journal of Physical Chemistry, Vol. 100, Issue 16 https://doi.org/10.1021/jp952678k	journal	January 1996
C−H Bond Activation and Organometallic Intermediates on Isolated Metal Centers on Oxide Surfaces Coperet, Christophe Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900122p	journal	February 2010
Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin Liu, W.; Huang, X.; Cheng, M. -J. Science, Vol. 337, Issue 6100 https://doi.org/10.1126/science.1222327	journal	September 2012
Methane vs benzene activation via transient tantalum amido-imido complex tert-Bu3SiNHTa(:NSiBu3-tert)2: structure of (py)2MeTa(:NSiBu3-tert)2 Schaller, Christopher P.; Wolczanski, Peter T. Inorganic Chemistry, Vol. 32, Issue 2 https://doi.org/10.1021/ic00054a005	journal	January 1993
Variable Pathways for Oxygen Atom Insertion into Metal–Carbon Bonds: The Case of Cp*W(O) ₂ (CH ₂ SiMe ₃ ) Mei, Jiajun; Carsch, Kurtis M.; Freitag, Cody R. Journal of the American Chemical Society, Vol. 135, Issue 1 https://doi.org/10.1021/ja309755g	journal	December 2012
Net Hydrogenation of Pt−NHPh Bond Is Catalyzed by Elemental Pt Webb, Joanna R.; Pierpont, Aaron W.; Munro-Leighton, Colleen Journal of the American Chemical Society, Vol. 132, Issue 13 https://doi.org/10.1021/ja9102309	journal	March 2010
Intermolecular C–H bond activation of benzene and pyridines by a vanadium(iii) alkylidene including a stepwise conversion of benzene to a vanadium-benzyne complex Andino, José G.; Kilgore, Uriah J.; Pink, Maren Chemical Science, Vol. 1, Issue 3 https://doi.org/10.1039/c0sc00201a	journal	January 2010
Aliphatic hydroxylation via oxygen rebound. Oxygen transfer catalyzed by iron Groves, John T.; McClusky, Gary A. Journal of the American Chemical Society, Vol. 98, Issue 3 https://doi.org/10.1021/ja00419a049	journal	February 1976
Flavin-Catalyzed Insertion of Oxygen into Rhenium–Methyl Bonds Pouy, Mark J.; Milczek, Erika M.; Figg, Travis M. Journal of the American Chemical Society, Vol. 134, Issue 31 https://doi.org/10.1021/ja3054139	journal	July 2012
Investigation of the Mechanism of Alkane Reductive Elimination and Skeletal Isomerization in Tp‘Rh(CNneopentyl)(R)H Complexes: The Role of Alkane Complexes Northcutt, Todd O.; Wick, Douglas D.; Vetter, Andrew J. Journal of the American Chemical Society, Vol. 123, Issue 30 https://doi.org/10.1021/ja003944x	journal	August 2001
Synthesis and reactivity of ruthenium amide-phosphine complexes. Facile conversion of a ruthenium amide to a ruthenium amine via dihydrogen activation and orthometalation. X-ray structure of RuCl(C6H4PPh2)[NH(SiMe2CH2PPh2)2] Fryzuk, Michael D.; Montgomery, Craig D.; Rettig, Steven J. Organometallics, Vol. 10, Issue 2 https://doi.org/10.1021/om00048a025	journal	February 1991
Synthesis and Reactivity of a Coordinatively Unsaturated Ruthenium(II) Parent Amido Complex: Studies of X−H Activation (X = H or C) Conner, David; Jayaprakash, K. N.; Cundari, Thomas R. Organometallics, Vol. 23, Issue 11 https://doi.org/10.1021/om049836r	journal	April 2004
Low-Coordinate Iron(II) Amido Complexes of β-Diketiminates: Synthesis, Structure, and Reactivity Eckert, Nathan A.; Smith, Jeremy M.; Lachicotte, Rene J. Inorganic Chemistry, Vol. 43, Issue 10 https://doi.org/10.1021/ic035483x	journal	May 2004
Hydrocarbon Hydroxylation by Cytochrome P450 Enzymes Ortiz de Montellano, Paul R. Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr9002193	journal	February 2010
Key elements of the chemistry of cytochrome P-450: The oxygen rebound mechanism Groves, John T. Journal of Chemical Education, Vol. 62, Issue 11 https://doi.org/10.1021/ed062p928	journal	November 1985
Structure and chemistry of bis(cyclopentadienyl)-MLn complexes Lauher, Joseph W.; Hoffmann, Roald Journal of the American Chemical Society, Vol. 98, Issue 7 https://doi.org/10.1021/ja00423a017	journal	March 1976
Experimental and Computational Studies of Ruthenium(II)-Catalyzed Addition of Arene C−H Bonds to Olefins Lail, Marty; Bell, Christen M.; Conner, David Organometallics, Vol. 23, Issue 21 https://doi.org/10.1021/om049404g	journal	October 2004
C−H Bond Activation by Rhodium(I) Phenoxide and Acetate Complexes: Mechanism of H−D Exchange between Arenes and Water Hanson, Susan Kloek; Heinekey, D. Michael; Goldberg, Karen I. Organometallics, Vol. 27, Issue 7 https://doi.org/10.1021/om7012259	journal	April 2008
Small molecule elimination from Group IVB (titanium, zirconium, hafnium) amido complexes Cundari, Thomas R.; Gordon, Mark S. Journal of the American Chemical Society, Vol. 115, Issue 10 https://doi.org/10.1021/ja00063a044	journal	May 1993
Reactivity of Ruthenium(II) and Copper(I) Complexes that Possess Anionic Heteroatomic Ligands: Synthetic Exploitation of Nucleophilicity and Basicity of Amido, Hydroxo, Alkoxo, and Aryloxo Ligands for the Activation of Substrates that Possess Polar Bonds as well as Nonpolar C–H and H–H Bonds Gunnoe, T. Brent European Journal of Inorganic Chemistry, Vol. 2007, Issue 9 https://doi.org/10.1002/ejic.200601072	journal	March 2007
C−H Bond Activations by Metal Oxo Compounds Gunay, Ahmet; Theopold, Klaus H. Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900269x	journal	February 2010
Hydrogen Atom Abstraction by Metal−Oxo Complexes: Understanding the Analogy with Organic Radical Reactions Mayer, James M. Accounts of Chemical Research, Vol. 31, Issue 8 https://doi.org/10.1021/ar970171h	journal	August 1998
Acceleration of Nucleophilic CH Activation by Strongly Basic Solvents Hashiguchi, Brian G.; Young, Kenneth J. H.; Yousufuddin, Muhammed Journal of the American Chemical Society, Vol. 132, Issue 36 https://doi.org/10.1021/ja102518m	journal	September 2010
Coinage Metal Catalyzed C−H Bond Functionalization of Hydrocarbons Díaz-Requejo, M. Mar; Pérez, Pedro J. Chemical Reviews, Vol. 108, Issue 8 https://doi.org/10.1021/cr078364y	journal	August 2008
Mechanism of Homogeneous Ir(III) Catalyzed Regioselective Arylation of Olefins Oxgaard, Jonas; Muller, Richard P.; Goddard, William A. Journal of the American Chemical Society, Vol. 126, Issue 1 https://doi.org/10.1021/ja034126i	journal	January 2004
Addition of Arenes to Ethylene and Propene Catalyzed by Ruthenium Lail, Marty; Arrowood, Benjamin N.; Gunnoe, T. Brent Journal of the American Chemical Society, Vol. 125, Issue 25 https://doi.org/10.1021/ja035076k	journal	June 2003
CH Bond Activation by Rhodium(I) Hydroxide and Phenoxide Complexes Kloek, Susan M.; Heinekey, D. Michael; Goldberg, Karen I. Angewandte Chemie International Edition, Vol. 46, Issue 25 https://doi.org/10.1002/anie.200700270	journal	June 2007
C−H Activation for the Construction of C−B Bonds Mkhalid, Ibraheem A. I.; Barnard, Jonathan H.; Marder, Todd B. Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900206p	journal	February 2010
Homogeneous Oxidation of Alkanes by Electrophilic Late Transition Metals Stahl, Shannon S.; Labinger, Jay A.; Bercaw, John E. Angewandte Chemie International Edition, Vol. 37, Issue 16 https://doi.org/10.1002/(SICI)1521-3773(19980904)37:16<2180::AID-ANIE2180>3.0.CO;2-A	journal	September 1998
Benzene C−H Bond Activation in Carboxylic Acids Catalyzed by O-Donor Iridium(III) Complexes: An Experimental and Density Functional Study Bischof, Steven M.; Ess, Daniel H.; Meier, Steven K. Organometallics, Vol. 29, Issue 4 https://doi.org/10.1021/om900036j	journal	January 2010
Catalytic CH Amination with Unactivated Amines through Copper(II) Amides Wiese, Stefan; Badiei, Yosra M.; Gephart, Raymond T. Angewandte Chemie International Edition, Vol. 49, Issue 47 https://doi.org/10.1002/anie.201003676	journal	September 2010
Arene C–H bond activation across Pt( ii )–OH bonds: catalyzed vs. uncatalyzed pathways Lohr, Tracy L.; Piers, Warren E.; Parvez, Masood Chem. Sci., Vol. 4, Issue 2 https://doi.org/10.1039/C2SC21917D	journal	January 2013
Catalytic Cycle for the Asymmetric Hydrogenation of Prochiral Ketones to Chiral Alcohols: Direct Hydride and Proton Transfer from Chiral Catalysts trans -Ru(H) ₂ (diphosphine)(diamine) to Ketones and Direct Addition of Dihydrogen to the Resulting Hydridoamido Complexes Abdur-Rashid, Kamaluddin; Faatz, Michael; Lough, Alan J. Journal of the American Chemical Society, Vol. 123, Issue 30 https://doi.org/10.1021/ja015902u	journal	August 2001

Journal Article · Wed Jul 05 00:00:00 EDT 1989 · Journal of the American Chemical Society; (USA) · OSTI ID:1382880

Chisholm, M H; Huffman, J C; Hampden-Smith, M J

Dehydrofluorination of Hydrofluorocarbons by Titanium Alkylidynes via Sequential C-H/C-F Bond Activation Reactions. A Synthetic, Structural, and Mechanistic Study of 1,2-CH Bond Addition and [beta]-Fluoride Elimination

Journal Article · Wed Jan 07 00:00:00 EST 2009 · Organometallics · OSTI ID:1382880

Fout, A R; Scott, J; Miller, D L; +3 more

Variable Pathways for Oxygen Atom Insertion into Metal–Carbon Bonds: The Case of Cp*W(O) ₂ (CH ₂ SiMe ₃ )

Journal Article · Fri Dec 21 00:00:00 EST 2012 · Journal of the American Chemical Society · OSTI ID:1382880

Mei, Jiajun; Carsch, Kurtis M.; Freitag, Cody R.; +2 more

Related Subjects

catalysis (homogeneous)
catalysis (heterogeneous)
bio-inspired
hydrogen and fuel cells
materials and chemistry by design
synthesis (novel materials)

Title: Activation of carbon–hydrogen bonds and dihydrogen by 1,2-CH-addition across metal–heteroatom bonds

Citation Formats

References (113)

Similar Records

Related Subjects