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1 Scifinder Scholar Oxid Addn Eta 2 Refs 4 January 2008 SciFinder Scholar Page: 1 oxid addn eta 2 refs Research Topic task started on Fri Jan 4, 2008 at 4:17 PM 5 Research Topic candidates were identified in CAPLUS and MEDLINE. using the phrase "oxidative addition and mechanism" Selected 2 of 5 candidate topics. 5 references were found containing "oxidative addition and mechanism" as entered. 11860 references were found containing both of the concepts "oxidative addition" and "mechanism". Research Topic Refine started 154 references were found when refined using the phrase "benzene and complex" Connected to ChemPort: document * Liu, Weijun, Welch, Kevin, Trindle, Carl O., Sabat, Michal, Myers, William H., Harman, W. Dean. Facile Intermolecular Aryl-F Bond Cleavage in the Presence of Aryl C-H Bonds: Is the ? 2-Arene Intermediate Bypassed?. Organometallics (2007), 26 (10), 2589-2597. Connected to ChemPort: document * Green, Jennifer C., Herbert, Benjamin J., Lonsdale, Richard. Oxidative addition of aryl chlorides to palladium N-heterocyclic carbene complexes and their role in catalytic arylamination. Journal of Organometallic Chemistry (2005), 690 (24-25), 6054-6067. Copyrights: CAPLUS: Copyright © 2007 American Chemical Society. All Rights Reserved. (The UK patent material in this product/service is UK Crown copyright and is made available with permission. © Crown Copyright. The French (FR) patent material in this product/service is made available from Institut National de la Propriete Industrielle (INPI).) MEDLINE: Produced by the U.S. National Library of Medicine REGISTRY: Copyright © 2007 American Chemical Society. All Rights Reserved. (Some records contain information from GenBank(R). See also: Benson D.A., Karsch-Mizrachi I., Lipman D.J., Ostell J., Rapp B.A., Wheeler D.L. Genbank. Nucl. Acids Res. 28(1):15-18 (2000). Property values tagged with IC are from the ZIC/VINITI data file provided by InfoChem.) CAS Registry is a service mark of the American Chemical Society. CASREACT: Copyright © 2007 American Chemical Society. All Rights Reserved. (In addition to reactions indexed by CAS, CASREACT contains reactions derived from the following sources: ZIC/VINITI database (1974-1999) provided by InfoChem, INPI data prior to 1986, and Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich.) CHEMLIST, CHEMCATS: Copyright © 2007 American Chemical Society. All Rights Reserved. Task History 4 January 2008 SciFinder Scholar Page: 2 oxid addn eta 2 refs Answer 1: Bibliographic Information Activation of carbon-hydrogen bonds via 1,2-addition across M-X (X = OH or NH2) bonds of d6 transition metals as a potential key step in hydrocarbon functionalization: a computational study. Cundari, Thomas R.; Grimes, Thomas V.; Gunnoe, T. Brent. Department of Chemistry and Center for Advanced Scientific Computing and Modeling (CASCaM), University of North Texas, Denton, TX, USA. Journal of the American Chemical Society (2007), 129(43), 13172-13182. Publisher: American Chemical Society, CODEN: JACSAT ISSN: 0002-7863. Journal written in English. CAN 148:33871 AN 2007:1141297 CAPLUS (Copyright (C) 2007 ACS on SciFinder (R)) Abstract Potential energy surfaces for oxidative addn. of benzene C-H-bonds to triazoborate d6-transition metal complexes [[HB(N:NH-? -N)3]M(X)(PH3)2]q (X = OH, NH2; M = Tc, Re, q = -1; M = Ru, q = 0; M = Co, Ir, q = +1; M = Ni, Pt, q = +2) were calcd. at DFT B3LYP level. The benzene activation started by formation of active species [[HB(N:NH-? -N)3]M(X)(PH3)]q (B) and proceeds via formation of the benzene ?-complexes [[HB(N:NH-? -N)3]M(X)(PH3)(? -C6H6)]q (C), oxidative addn. to form Ph complexes [[HB(N:NH-? -N)3]M(X)(PH3)(Ph)(XH)] (E) and ligand substitution to give the products [[HB(N:NH-? -N)3]M(X)(PH3)2(Ph)] (F). For the benzene C-H activation reaction steps, kite-shaped transition states were located and found to have relatively little metal-hydrogen interaction. The C-H activation process is best described as a metal-mediated proton transfer in which the metal center and ligand X function as an activating electrophile and intramol. base, resp. While the metal plays a primary role in controlling the kinetics and thermodn. of the reaction coordinate for C-H activation/functionalization, the ligand X also influences the energetics. On the basis of three thermodn. criteria characterizing salient energetic aspects of the proposed catalytic cycle and the detailed computational studies reported herein, late transition metal complexes (e.g., Pt, Co, etc.) in the d6 electron configuration, esp. the [[HB(N:NH-? -N)3]Co(PH3)2(OH)]+ complex and related Co(III) systems, are predicted to be the most promising for further catalyst investigation. Answer 2: Bibliographic Information Competitive O-H and C-H oxidative addition of CH3OH to rhodium(ii) porphyrins. Li, Shan; Cui, Weihong; Wayland, Bradford B. Department of Chemistry, University of Pennsylvania, Philadelphia, PA, USA. Chemical Communications (Cambridge, United Kingdom) (2007), (39), 4024-4025. Publisher: Royal Society of Chemistry, CODEN: CHCOFS ISSN: 1359-7345. Journal written in English. CAN 148:23211 AN 2007:1108142 CAPLUS (Copyright (C) 2007 ACS on SciFinder (R)) Abstract Rhodium(ii) porphyrins react with CH3OH in benzene by alternate mechanisms that give H-CH2OH and H-OCH3 bond activation in different methanol concn. regimes which is a rare example of transition metal reactivity with methanol. Answer 3: Bibliographic Information Carbon-Hydrogen Bond Activation in Hydridotris(pyrazolyl)borate Platinum(IV) Complexes: Comparison of Density Functionals, Basis Sets, and Bonding Patterns. Vastine, Benjamin Alan; Webster, Charles Edwin; Hall, Michael B. Department of Chemistry, Texas A&M University, College Station, TX, USA. Journal of Chemical Theory and Computation (2007), 3(6), 2268-2281. Publisher: American Chemical Society, CODEN: JCTCCE ISSN: 1549-9618. Journal written in English. CAN 147:522379 AN 2007:1033046 CAPLUS (Copyright (C) 2007 ACS on SciFinder (R)) 4 January 2008 SciFinder Scholar Page: 3 oxid addn eta 2 refs Abstract The reaction mechanism for the cycle beginning with the reductive elimination (RE) of methane from ? 3-TpPtIV(CH3)2H (1) (Tp = hydridotris(pyrazolyl)borate) and subsequent oxidative addn. (OA) of benzene to form finally ? 3-TpPtIV(Ph)2H (19) was investigated by d. functional theory (DFT). Two mechanistic steps are of particular interest, namely the barrier to C-H coupling (barrier 1 - Ba1) and the barrier to methane release (barrier 2 - Ba2). For 31 d. functionals, the calcd. values for Ba1 and Ba2 were benchmarked against the exptl. reported values of 26 (Ba1) and 35 (Ba2) kcal?mol-1, resp. Specifically, the values for Ba1 and Ba2, calcd. at the B3LYP/double-? plus polarization level of theory, are 24.6 and 34.3 kcal?mol-1, resp. Overall, the best performing functional was BPW91 where the mae assocd. with the calcd. values of the two barriers is 0.68 kcal?mol-1. The calcd. B3LYP values of Ba1 ranged between 20 and 26 kcal?mol-1 for 12 effective core potential basis sets for platinum and 29 all-electron basis sets for the first row elements. Polarization functions for the first row elements were important for accurate values, but the addn. of diffuse functions to non-hydrogen (+) and hydrogen atoms (++) had little effect on the calcd. values. Basis set satn. was achieved with APNO basis sets utilized for first-row atoms. Bader's "Atoms in Mols." was used to analyze the electron d. of several complexes, and the electron d. at the Pt-Nax bond crit. point (trans to the active site for C-H coupling) varied over a wider range than any of the other Pt-N bonds. Answer 4: Bibliographic Information Investigations Directed at Catalytic Carbon-Carbon and Carbon-Oxygen Bond Formation via C-H Bond Activation. Blackmore, Ian J.; Semiao, Christopher J.; Buschhaus, Miriam S. A.; Patrick, Brian O.; Legzdins, Peter. Department of Chemistry, The University of British Columbia, Vancouver, BC, Can. Organometallics (2007), 26(20), 4881-4889. Publisher: American Chemical Society, CODEN: ORGND7 ISSN: 0276-7333. Journal written in English. CAN 147:427460 AN 2007:921226 CAPLUS (Copyright (C) 2007 ACS on SciFinder (R)) Abstract A potential catalytic cycle for the arom. C-H-bond activation by molybdenum and tungsten half-sandwich nitrosyl complexes Cp'M(NO)(L) (M = Mo, W; Cp' = ? 5-C5Me5, ? 5-C5H5; L = Lewis base) was explored by NMR monitoring, isolation and structural characterization of intermediates. The cycle is based on three steps: (1) oxidative addn. of the hydrocarbon substrate to the metal center, (2) subsequent hydrometalation of the olefin or the ketone, and (3) final reductive elimination of the coupled product. Of the various Cp'M(NO)(L) groups examd., the Cp*W(NO)(PPh3) fragment has been found to be the best candidate for mediating these catalytic steps since it is not prone to form unreactive Cp*W(NO)(PPh3)2 as are some of the other fragments that readily decomp. to 18e Cp'M(NO)L2 complexes. Hence, Cp*W(NO)(PPh3) has been utilized to det. if the oxidative addn. and hydrometalation steps can occur sequentially under one-pot exptl. conditions. However, olefins are too ?-acidic and readily form stable 18e Cp*W(NO)(PPh3)(? 2-olefin) adducts, which prevent oxidative addn. of the hydrocarbon substrate to the tungsten center. Similarly, benzophenone, Ph2CO, and diisopropyl ketone, iPr2CO, also form 1:1 ? 2-C:O adducts with the ?-basic tungsten center in the 16e fragment. Nevertheless, oxidative addn. and hydrometalation do occur sequentially to form the desired aryl alkoxide complex, Cp*W(NO)(OCHiPr2)(Ph), in addn. to the Cp*W(NO)(? 2-OCiPr2)(PPh3) adduct, when benzene and diisopropyl ketone are employed as the two substrates. The solid-state mol. structures of cis-Cp*W(NO)[? 2-(CH2NMe)P(NMe2)2](H), Cp*W(NO)(OCHiPr2)(Ph), and Cp*W(NO)(? 2-OCiPr2)(PPh3) have been established by single-crystal x-ray crystallog.
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