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Photochemical Metal-to-Oxo Migrations of Aryl and Alkyl Ligands

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    Photochemical Metal-to-Oxo Migrations of Aryl and Alkyl Ligands
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    Organometallics

    Cite this: Organometallics 1995, 14, 6, 2951–2960
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    https://doi.org/10.1021/om00006a045
    Published June 1, 1995
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    Cited By

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    This article is cited by 40 publications.

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    2. Glenn R. Morello and Thomas R. Cundari . Density Functional Study of Oxygen Insertion into Niobium–Phosphorus Bonds: Novel Mechanism for Liberating P3– Synthons. Organometallics 2016, 35 (20) , 3624-3634. https://doi.org/10.1021/acs.organomet.6b00679
    3. Leila G. Ranis, Kalpani Werellapatha, Nicholas J. Pietrini, Bruce A. Bunker, and Seth N. Brown . Metal and Ligand Effects on Bonding in Group 6 Complexes of Redox-Active Amidodiphenoxides. Inorganic Chemistry 2014, 53 (19) , 10203-10216. https://doi.org/10.1021/ic501222n
    4. Dale R. Pahls, John T. Groves, T. Brent Gunnoe, and Thomas R. Cundari . Theoretical Study of Reductive Functionalization of Methyl Ligands of Group 9 Complexes Supported by Two Bipyridyl Ligands: A Key Step in Catalytic Hydrocarbon Functionalization. Organometallics 2014, 33 (8) , 1936-1944. https://doi.org/10.1021/om4010093
    5. Daniel B. Pardue, Jiajun Mei, Thomas R. Cundari, and T. Brent Gunnoe . Density Functional Theory Study of Oxygen-Atom Insertion into Metal–Methyl Bonds of Iron(II), Ruthenium(II), and Osmium(II) Complexes: Study of Metal-Mediated C–O Bond Formation. Inorganic Chemistry 2014, 53 (6) , 2968-2975. https://doi.org/10.1021/ic402759w
    6. Travis M. Figg and Thomas R. Cundari . Mechanistic Study of Oxy Insertion into Nickel–Carbon Bonds with Nitrous Oxide. Organometallics 2012, 31 (14) , 4998-5004. https://doi.org/10.1021/om300270x
    7. Travis M. Figg, Joanna R. Webb, Thomas R. Cundari, and T. Brent Gunnoe . Carbon–Oxygen Bond Formation via Organometallic Baeyer–Villiger Transformations: A Computational Study on the Impact of Metal Identity. Journal of the American Chemical Society 2012, 134 (4) , 2332-2339. https://doi.org/10.1021/ja2102778
    8. Travis M. Figg, Thomas R. Cundari, and T. Brent Gunnoe . Non-redox Oxy-Insertion via Organometallic Baeyer–Villiger Transformations: A Computational Hammett Study of Platinum(II) Complexes. Organometallics 2011, 30 (14) , 3779-3785. https://doi.org/10.1021/om200258d
    9. Steven M. Bischof, Mu-Jeng Cheng, Robert J. Nielsen, T. Brent Gunnoe, William A. Goddard, III, and Roy A. Periana . Functionalization of Rhenium Aryl Bonds by O-Atom Transfer. Organometallics 2011, 30 (8) , 2079-2082. https://doi.org/10.1021/om2002365
    10. Joseph M. Keane, , W. Dean Harman. A New Generation of π-Basic Dearomatization Agents. Organometallics 2005, 24 (8) , 1786-1798. https://doi.org/10.1021/om050029h
    11. António Paulo,, Ângela Domingos,, Raquel Garcia, and, Isabel Santos. Cationic Re(V) Oxo Complexes with Poly(pyrazolyl)borates:  Synthesis, Characterization, and Stability. Inorganic Chemistry 2000, 39 (25) , 5669-5674. https://doi.org/10.1021/ic000481n
    12. T. Brent Gunnoe,, Scott H. Meiere,, Michal Sabat, and, W. Dean Harman. {TpRe(bpy)}:  A Novel Pentaaminerhenium System That Stabilizes Both High and Low Oxidation States (Tp = Hydridotris(pyrazolyl)borate; bpy = 2,2‘-Bipyridyl). Inorganic Chemistry 2000, 39 (26) , 6127-6130. https://doi.org/10.1021/ic000707m
    13. Marianne P. Wilkerson,, Carol J. Burns,, Harry J. Dewey,, Jerod M. Martin,, David E. Morris,, Robert T. Paine, and, Brian L. Scott. Basicity of Uranyl Oxo Ligands upon Coordination of Alkoxides. Inorganic Chemistry 2000, 39 (23) , 5277-5285. https://doi.org/10.1021/ic000142u
    14. T. Brent Gunnoe,, Michal Sabat, and, W. Dean Harman. Stereoselective Dihapto-Binding of Prochiral Aromatic Compounds by {TpRe(CO)(PMe3)}:  Synthesis, Characterization, Stability, and Enantiofacial Discrimination (Tp = Hydrido(tris)pyrazolylborate). Organometallics 2000, 19 (5) , 728-740. https://doi.org/10.1021/om9906722
    15. K. Rajender Reddy,, Ângela Domingos,, António Paulo, and, Isabel Santos. Rhenium(V) Dioxo Complexes with Dihydrobis(pyrazolyl)borates:  Synthesis and Reactivity toward Electrophilic Substrates. Inorganic Chemistry 1999, 38 (19) , 4278-4282. https://doi.org/10.1021/ic990229j
    16. T. Brent Gunnoe,, Michal Sabat, and, W. Dean Harman. Enantiofacial Discrimination in Dihapto-Coordination of Aromatic Molecules by the Chiral π-Base/σ-Lewis Acid {TpRe(CO)(PMe3)}. Journal of the American Chemical Society 1999, 121 (27) , 6499-6500. https://doi.org/10.1021/ja990891e
    17. T. Brent Gunnoe,, Michal Sabat, and, W. Dean Harman. Reactions of TpRe(CO)2(THF) with Aromatic Molecules (Tp = Hydridotris(pyrazolyl)borate). Journal of the American Chemical Society 1998, 120 (34) , 8747-8754. https://doi.org/10.1021/ja980690v
    18. Yun Chi,, Hsiao-Ling Wu,, Chi-Chung Chen,, Chi-Jung Su,, Shie-Ming Peng, and, Gene-Hsiang Lee. Syntheses and Reactivity of Heterometallic Oxo−Acetylide Cluster Compounds. Skeletal Rearrangement and Conversion of Acetylide to Alkenyl, Alkylidene, and Allenyl Ligands on a WRe2 Framework. Organometallics 1997, 16 (11) , 2434-2442. https://doi.org/10.1021/om9609426
    19. Waldemar Adam,, Jürgen Putterlik,, Rosemarie M. Schuhmann, and, Jörg Sundermeyer. Synthesis of Tris(pyrazolyl)borate-Stabilized Vinyl, Allyl, and Homoallyl Tungsten Oxides and Their Selective Oxyfunctionalization by Singlet Oxygen and Dioxirane. Organometallics 1996, 15 (21) , 4586-4596. https://doi.org/10.1021/om960366d
    20. Courtney L. Baumberger, Victoria Z. Valley, Matthew B. Chambers. Direct photocatalytic C–H functionalization mediated by a molybdenum dioxo complex. Chemical Communications 2024, 60 (54) , 6901-6904. https://doi.org/10.1039/D4CC01789G
    21. Julia A. Edwards, Jeffrey N. Templeton, Christopher J.A. Daley, Lisa F. Szczepura. Coordination of apical O- and S-donor ligands to the hexarhenium(III) cluster core: Investigating the electrochemistry of alcoholate containing cluster complexes. Inorganica Chimica Acta 2024, 563 , 121905. https://doi.org/10.1016/j.ica.2023.121905
    22. Saeed Fosshat, Frank R. Fronczek, Matthew B. Chambers. The Role of Anionic Ligands on Photoreactivity in Mo(VI) Dioxo Complexes of the Form MoO 2 X 2 (NN)**. Chemistry – A European Journal 2023, 29 (29) https://doi.org/10.1002/chem.202300486
    23. Mu-Jeng Cheng, Robert J. Nielsen, William A. Goddard III. A homolytic oxy-functionalization mechanism: intermolecular hydrocarbyl migration from M–R to vanadate oxo. Chem. Commun. 2014, 50 (75) , 10994-10996. https://doi.org/10.1039/C4CC03067B
    24. Joanna R. Webb, Travis M. Figg, Brooke M. Otten, Thomas R. Cundari, T. Brent Gunnoe, Michal Sabat. Pt II and Rh III Hydrocarbyl Complexes Bearing Coordinated Oxygen Atom Delivery Reagents. European Journal of Inorganic Chemistry 2013, 2013 (25) , 4515-4525. https://doi.org/10.1002/ejic.201300434
    25. Travis M. Figg, Thomas R. Cundari. Computational Hammett analysis of redox based oxy-insertion by Pt( ii ) complexes. Dalton Trans. 2013, 42 (12) , 4114-4121. https://doi.org/10.1039/C2DT31983G
    26. A. Yu. Ledneva, N. G. Naumov, A. V. Virovets, S. Cordier, Y. Molard. Crystal structures of trans-[Re6S8(CN)2L4] complexes, L = pyridine or 4-methylpyridine. Journal of Structural Chemistry 2012, 53 (1) , 132-137. https://doi.org/10.1134/S0022476612010179
    27. Joanna R. Webb, Tamara Bolaño, T. Brent Gunnoe. Catalytic Oxy‐Functionalization of Methane and Other Hydrocarbons: Fundamental Advancements and New Strategies. ChemSusChem 2011, 4 (1) , 37-49. https://doi.org/10.1002/cssc.201000319
    28. Marty Lail, Karl A. Pittard, T. Brent Gunnoe. Chemistry Surrounding Group 7 Complexes that Possess Poly(pyrazolyl)borate Ligands. 2008, 95-153. https://doi.org/10.1016/S0065-3055(07)56002-8
    29. T. Brent Gunnoe. 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. European Journal of Inorganic Chemistry 2007, 2007 (9) , 1185-1203. https://doi.org/10.1002/ejic.200601072
    30. António Paulo, João D.G. Correia, Maria P.C. Campello, Isabel Santos. A short ride on scorpionates: from d- to f-elements. Polyhedron 2004, 23 (2-3) , 331-360. https://doi.org/10.1016/j.poly.2003.11.022
    31. Jörg Sundermeyer. The Metal‐Mediated Oxidation of Organic Substrates via Organometallic Intermediates: Recent Developments and Questions of Dispute. 2003, 133-139. https://doi.org/10.1002/9783527620784.ch23b
    32. Raquel Garcia, Yong Heng Xing, Ângela Domingos, António Paulo, Isabel Santos. Rhenium oxocomplexes with the heteroscorpionate phenyltris(pyrazolyl)borate: synthesis and structural studies. Inorganica Chimica Acta 2003, 343 , 27-32. https://doi.org/10.1016/S0020-1693(02)01184-2
    33. Scott H. Meiere, W. Dean Harman. TpRe(L)(Br) 2 (Tp = hydridotris(pyrazolyl)borate); L =  t BuNC, PMe 3 , pyridine (py), 1-methylimidazole (MeIm)). 2002https://doi.org/10.1002/047084289X.rn00169
    34. D.C. Bradley, R.C. Mehrotra, I.P. Rothwell, A. Singh. Metal Aryloxides. 2001, 445-669. https://doi.org/10.1016/B978-012124140-7/50006-2
    35. Benjamin C. Brooks, T. Brent Gunnoe, W. Dean Harman. Dihapto binding of aromatic molecules by π-basic transition metal complexes: development of alternatives to the {Os(NH3)5}2+ fragment. Coordination Chemistry Reviews 2000, 206-207 , 3-61. https://doi.org/10.1016/S0010-8545(99)00249-0
    36. Brian K. Bennett, Thomas J. Crevier, Darin D. DuMez, Yoshihiro Matano, W.Stephen McNeil, James M. Mayer. Electrochemical and reactivity comparisons among isoelectronic oxo, imido, and nitrido complexes of rhenium and osmium. Journal of Organometallic Chemistry 1999, 591 (1-2) , 96-103. https://doi.org/10.1016/S0022-328X(99)00506-9
    37. Jörg Sundermeyer. The Metal‐Mediated Oxidation of Organic Substrates via Organometallic Intermediates: Recent Developments and Questions of Dispute. 1998, 133-139. https://doi.org/10.1002/9783527619962.ch23
    38. Kevin P. Gable. Rhenium and Technetium Oxo Complexes in the Study of Organic Oxidation Mechanisms. 1997, 127-161. https://doi.org/10.1016/S0065-3055(08)60438-4
    39. Colin S. Masui, James M. Mayer. Imido and amido complexes of hydrotris(pyrazolyl)borate-rhenium. Inorganica Chimica Acta 1996, 251 (1-2) , 325-333. https://doi.org/10.1016/S0020-1693(96)05286-3
    40. Klaus H. Theopold. Dioxygen Activation by Organometallics of Early Transition Metals. , 17-37. https://doi.org/10.1007/3418_038
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    Organometallics

    Cite this: Organometallics 1995, 14, 6, 2951–2960
    Click to copy citationCitation copied!
    https://doi.org/10.1021/om00006a045
    Published June 1, 1995
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