Studies on gas-phase cyclometalations of [ArNi(PPh3)n]+ (n = 1 or 2) by electrospray ionization tandem mass spectrometry
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  • 作者:Jing Zhou (1)
    Qian Zhao (2)
    Wen-Wen Chen (2)
    Haoyang Wang (1)
    Guo-Qiang Lin (2)
    Ming-Hua Xu (2)
    Yinlong Guo (1)
  • 刊名:Journal of The American Society for Mass Spectrometry
  • 出版年:2010
  • 出版时间:July 2010
  • 年:2010
  • 卷:21
  • 期:7
  • 页码:1265-1274
  • 全文大小:814KB
  • 参考文献:1. Bruce, M. I. Cyclometalation Reactions. / Angew. Chem. Int. Ed. Engl. 1977, / 16(2), 73鈥?6. CrossRef
    2. Dehand, J.; Pfeffer, M. Cyclometalated Compounds / Coord. / Chem. Rev. 1976, / 18(3), 327鈥?52.
    3. Omae, I. Organometallic Intramolecular-Coordination Compounds Containing a Phosphorus Donor Ligand / Coord. / Chem. Rev. 1980, / 32(3), 235鈥?71.
    4. Rothwell, I. P. Carbon Hydrogen Bond Activation in Early Transition-Metal Systems. / Polyhedron 1985, / 4(2), 177鈥?00. CrossRef
    5. Newkome, G. R.; Puckett, W. E.; Gupta, V. K.; Kiefer, G. E. Cyclometalation of the Platinum Metals with Nitrogen and Alkyl, Alkenyl, and Benzyl Carbon Donors. / Chem. Rev. 1986, / 86(2), 451鈥?89. CrossRef
    6. Omae, I. Recent Studies on Organometallic Intramolecular-Coordination Compounds. / Coord. Chem. Rev. 1988, / 83, 137鈥?67. CrossRef
    7. Omae, I. Intramolecular Five-Membered Ring Compounds and Their Applications. / Coord. Chem. Rev. 2004, / 248(11/12), 995鈥?023. CrossRef
    8. Sokolov, V. I. Asymmetric Cyclopalladation as a Tool of Enantioselective Synthesis. / Pure Appl. Chem. 1983, / 55(11), 1837鈥?844. CrossRef
    9. Ryabov, A. D. Cyclopalladated Complexes in Organic-Synthesis. / Synthesis-Stuttgart 1985, / 1985(3), 233鈥?52. CrossRef
    10. Lewis, L. N. Enhancement of Catalytic Activity Through Orthometalation. Synthesis, Structure, and Catalytic Activity of a New Orthometalated Ruthenium Complex. / J. Am. Chem. Soc. 1986, / 108(4), 743鈥?49. CrossRef
    11. Lewis, L. N.; Smith, J. F. Catalytic Carbon-Carbon Bond Formation Via Orthometalated Complexes. / J. Am. Chem. Soc. 1986, / 108(10), 2728鈥?735. CrossRef
    12. Baratta, W.; da Ros, P.; Del Zotto, A.; Sechi, A.; Zangrando, E.; Rigo, P. Cyclometalated Ruthenium(II) Complexes as Highly Active Transfer Hydrogenation Catalysts. / Angew. Chem. Int. Ed. 2004, / 43(27), 3584鈥?588. CrossRef
    13. Maestri, M.; Sandrini, D.; Balzani, V.; Vonzelewsky, A.; Jolliet, P. Spectroscopic and Electrochemical Behavior of Cyclometalated Pd(II) Complexes / Helv. / Chim. Acta 1988, / 71(1), 134鈥?39. CrossRef
    14. Craig, C. A.; Watts, R. J. Photophysical Investigation of Palladium(II) Orthometalated Complexes. / Inorg. Chem. 1989, / 28(2), 309鈥?13. CrossRef
    15. Albrecht, M.; van Koten, G. Platinum Group Organometallics Based on 鈥淧incer鈥?Complexes: Sensors, Switches, and Catalysts. / Angeio. Chem. Int. Ed. 2001, / 40(20), 3750鈥?781. CrossRef
    16. Ryabov, A. D. Mechanisms of Intramolecular Activation of C-H Bonds in Transition-Metal Complexes / Chem. Rev. 1990, / 90(2), 403鈥?24. CrossRef
    17. Shilov, A. E.; Shteinman, A. A. Activation of Saturated-Hydrocarbons by Metal Complexes in Solution. / Coord. Chem. Rev. 1977, / 24(2/3), 97鈥?43. CrossRef
    18. Zucca, A.; Stoccoro, S.; Cinellu, M. A.; Minghetti, G.; Manassero, M. Cyclometalated Derivatives of Rhodium(III). Activation of C(sp3)-H vs. C(sp2)-H bonds. / J. Chem. Soc. Ballon Trans. 1999, 3431鈥?437.
    19. Minghetti, G.; Stoccoro, S.; Cinellu, M. A.; Soro, B.; Zucca, A. Activation of a C-H Bond in a Pyridine Ring. Reaction of 6-Substituted 2,2鈥?Bipyridines with Methyl and Phenyl Platinum(II) Derivatives: N鈥?C(3)-鈥淩ollover鈥?Cyclometalation. / Organometallics 2003, / 22(23), 4770鈥?777. CrossRef
    20. Shilov, A. E.; Shul鈥檖in, G. B. Activation of C-H Bonds by Metal Complexes. / Chem. Rev. 1997, / 97(8), 2879鈥?932. CrossRef
    21. Lersch, M.; Tilset, M. Mechanistic Aspects of C-H Activation by Pt Complexes. / Chem. Rev. 2005, / 105(6), 2471鈥?526. CrossRef
    22. Bruce, M. I.; Goodall, B. L.; Stone, F. G. A. / ortho-Metalation of Azobenzenes鈥擬echanistic Results. / J. Chem. Soc. Chem. Commun. 1973, 558鈥?59.
    23. Bruce, M. I.; Goodall, B. L.; Stone, F. G. A. Cyclometalation Reactions. Part 17. Comparative Studies of the Manganation and Palladation of Some Substituted Azobenzenes. / J. Chem. Soc. Ballon Trans. 1978, 687鈥?4.
    24. Jones, W. D.; Feher, F. J. Comparative Reactivities of Hydrocarbon C-H Bonds with a Transition-Metal Complex / Acc. Chem. Res. 1989, / 22(3), 91鈥?00. CrossRef
    25. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Selective Intermolecular Carbon-Hydrogen Bond Activation by Synthetic Metal Complexes in Homogeneous Solution. / Acc. Chem. Res. 1995, / 28(3), 154鈥?62. CrossRef
    26. Blum, S. A.; Tan, K. L.; Bergman, R. G. Application of Physical Organic Methods to the Investigation of Organometallic Reaction Mechanisms. / J. Org. Chem. 2003, / 68(11), 4127鈥?137. CrossRef
    27. Cinellu, M. A.; Minghetti, G.; Banditelli, G.; Bandini, A. L.; Pelli, B.; Traldi, P. FAB Mass Spectrometry of Palladium(II) Derivatives with 1,4-Benzodiazepin-2 ones: Evidence of the Stability of Cyclometalated Species. / Inorg. Chim. Acta 1989, / 161(1), 57鈥?2. CrossRef
    28. Neo, K. E.; Neo, Y. C.; Chien, S. W.; Tan, G. K.; Wilkins, A. L.; Henderson, W.; Hor, T. S. A. PdCl[PPh2CH2CH2CHCH2CH2PPh2] as a Precursor to Homo- and Hetero-Metallic Species Directed by ESMS (Electrospray Ionization Mass Spectrometry). / Ballon Trans. 2004, (15), 2281鈥?287.
    29. Butschke, B.; Schlangen, M.; Schr枚der, D.; Schwarz, H. 鈥淩oll-over鈥?Cyclometalation of 2,2鈥?Bipyridine Platinum(II) Complexes in the Gas Phase: A Combined Experimental and Computational Study. / Chem. Eur. J. 2008, / 14, 11050鈥?1060. CrossRef
    30. Colton, R.; Dagostino, A.; Traeger, J. C. Electrospray Mass Spectrometry Applied Inorganic and Organometallic Chemistry. / Mass Spedrom. Rev. 1995, / 14(2), 79鈥?06. CrossRef
    31. Henderson, W.; Nicholson, B. K.; McCaffrey, L. J. Applications of Electrospray Mass Spectrometry in Organometallic Chemistry. / Polyhedron 1998, / 17(25/26), 4291鈥?313. CrossRef
    32. Traeger, J. C. Electrospray Mass Spectrometry of Organometallic Compounds. / Int. J. Mass Spedrom. 2000, / 200(1/3), 387鈥?01. CrossRef
    33. Santos, L. S.; Knaack, L.; Metzger, J. O. Investigation of Chemical Reactions in Solution Using API-MS. / Int. J. Mass Spedrom. 2005, / 246(1/3), 84鈥?04. CrossRef
    34. Zhang, D. X.; Tao, W. A.; Cooks, R. G. Chiral Resolution of D- and L-Amino Acids by Tandem Mass Spectrometry of Ni(II)-Bound Trimeric Complexes. / Int. J. Mass Spedrom. 2001, / 204(1/3), 159鈥?69. CrossRef
    35. Wee, S.; O鈥橦air, R. A. J.; McFadyen, W. D. Gas-Phase Ligand Loss and Ligand Substitution Reactions of Platinum(II) Complexes of Tridentate Nitrogen Donor Ligands. / Rapid Commun. Mass Spedrom. 2004, / 18(11), 1221鈥?226. CrossRef
    36. O鈥橦air, R. A. J.; Vrkic, A. K.; James, P. F. Gas-Phase Synthesis and Reactivity of the Organomagnesates [CH3MgL2](-) (L = Cl and O2CCH3): From Ligand Effects to Catalysis. / J. Am. Chem. Soc. 2004, / 126(38), 12173鈥?2183. CrossRef
    37. Bhaskar, G.; Chary, M. A.; Kumar, M. K.; Syamasundar, K.; Vairamani, M.; Prabhakar, S. Electrospray Ionization Studies of Transition-Metal Complexes of 2-AcetyIbenzimidazolethiosemicarbazone Using Collision-Induced Dissociation and Ion-Molecule Reactions. / Rapid Commun. Mass Spectrom. 2005, / 19(11), 1536鈥?544. CrossRef
    38. Bach, S. B. H.; Sepeda, T. G.; Merrill, G. N.; Walmsley, J. A. Complexes of Dibromo(Ethylenediamine)Palladium(II) Observed from Aqueous Solutions by Electrospray Mass Spectrometry. / J. Am. Soc. Mass Spectrom. 2005, / 16(9), 1461鈥?469. CrossRef
    39. Peng, W. P.; Goodwin, M. P.; Chen, H.; Cooks, R. G.; Wilker, J. Thermal Formation of Mixed-Metal Inorganic Complexes at Atmospheric Pressure. / Rapid Commun. Mass Spectrom. 2008, / 22(22), 3540鈥?548. CrossRef
    40. Wang, H. Y.; Metzger, J. O. ESI-MS Study on First-Generation Ruthenium Olefin Metathesis Catalysts in Solution: Direct Detection of the Catalytically Active 14-Electron Ruthenium Intermediate. / Organometallics 2008, / 27(12), 2761鈥?766. CrossRef
    41. Hong, R.; Hoen, R.; Zhang, J.; Lin, G. Q. Nickel-Catalyzed Ullmann-Type Coupling Reaction to Prepare Tetra-ortho-Substituted Biaryls. / Synlett 2001, / 2001(10), 1527鈥?530. CrossRef
    42. Lei, J. G.; Hong, R.; Yuan, S. G.; Lin, G. Q. Nickel-Catalyzed Tandem Reaction to Asymmetric Synthesis of Chiral Phthalides. / Synlett 2002, / 2002(6), 927鈥?30. CrossRef
    43. Chen, W. W.; Xu, M. H.; Lin, G. Q. Unusual Heterochiral Crystallization Tendency of 3-Arylphthalide Compounds in Non-Racemic Solution: Reinvestigation on Asymmetric Ni-Catalyzed Tandem Reaction of Substituted o-Halobenzaldehydes. / Tetrahedron Lett. 2007, / 48, 7508鈥?511. CrossRef
    44. Tamao, K. Discovery of the Cross-Coupling Reaction Between Grignard Reagents and C(Sp(2)) Halides Catalyzed by Nickel-Phosphine Complexes. / Proceedings of the International Symposium on 30 Years of the Cross-Coupling Reaction; Kyoto, Japan, July, 2001; p. 23鈥?6.
    45. Tamaru, Y. / Modem Organonickel Chemistry; Wiley-VCH: Weinheim, 2005; pp 41鈥?3.
    46. Semmelhack, M. F.; Helquist, P.; Jones, L. D.; Keller, L.; Mendelson, L.; Ryono, L. S.; Smith, J. G.; Stauffer, R. D. Reaction of Aryl and Vinyl Halides with Zerovalent Nickel-Preparative Aspects and the Synthesis of Alnusone. / J. Am. Chem. Soc. 1981, / 103(21), 6460鈥?471. CrossRef
    47. Vachet, R. W.; Hartman, J. R.; Gertner, J. W.; Callahan, J. H. Investigation of Metal Complex Coordination Structure Using Collision-Induced Dissociation and Ion-Molecule Reactions in a Quadrupole Ion Trap Mass Spectrometer. / Int. J. Mass Spectrom. 2001, / 204(1/3), 101鈥?12. CrossRef
    48. Zhang, Q.; Bowers, M. T. Activation of Methane by MH + (M = Fe, Co, and Ni): A Combined Mass Spectrometric and DFT Study. / J. Phys. Chem. A 2004, / 108(45), 9755鈥?761. CrossRef
    49. Schlangen, M.; Schroder, D.; Schwarz, H. Pronounced Ligand Effects and the Role of Formal Oxidation States in the Nickel-Mediated Thermal Activation of Methane. / Angew. Chem. Int. Ed. 2007, / 46(10), 1641鈥?644. CrossRef
    50. Schlangen, M.; Schwarz, H. Thermal Activation of Methane by Group 10 Metal Hydrides MH+: The Same and Not the Same. / Angew. Chem. Int. Ed. 2007, / 46(29), 5614鈥?617. CrossRef
    51. Armelin, M.; Schlangen, M.; Schwarz, H. On the Mechanisms of Degenerate Ligand Exchange in [M(CH3)]+/CH4 Couples (M=Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, Pt) as Explored by Mass Spectrometric and Computational Studies: Oxidative Addition/Reductive Elimination versus 蟽-Complex-Assisted Metathesis. / Chem. Eur. J. 2008, / 14(17), 5229鈥?236. CrossRef
    52. Venanzi, L. M. Tetrahedral nickel(II) Complexes and the Factors Determining Their Formation. Part I. Bistriphenylphosphine Nickel(II) Compounds. / J. Chem. Soc. 1958, 719鈥?24.
    53. Cotton, F. A.; Goodgame, D. M.; Faut, O. D. Preparation, Spectra, and Electronic Structures of Tetrahedral Nickel(II) Complexes Containing Triphenylphosphine and Halide Ions as Ligands. / J. Am. Chem. Soc. 1961, / 83(2), 344鈥?51. CrossRef
    54. Waters, T.; O鈥橦air, R. A. J.; Wedd, A. G. Catalytic Gas Phase Dehydration of Acetic Acid to Ketene. / Int. J. Mass Spectrom. 2003, / 228(2/3), 599鈥?11. CrossRef
    55. Afonso, C.; Riu, A.; Xu, Y.; Founder, F.; Tabet, J. C. Structural Characterization of Fatty Acids Cationized with Copper by Electrospray Ionization Mass Spectrometry Under Low-Energy Collision-Induced Dissociation. / J. Mass Spectrom. 2005, / 40(3), 342鈥?49. CrossRef
    56. Nuutinen, J. M. J.; Ratilainen, J.; Rissanen, K.; Vainiotalo, P. Mass Spectrometric Studies on Small Open-Chain Piperazine-Containing Ligands and Their Transition Metal Complexes. / J. Mass Spectrom. 2001, / 36(8), 902鈥?10. CrossRef
    57. Gerdes, G.; Chen, P. Cationic Platinum(II) Carboxylato Complexes are Competent in Catalytic Arene C-H Activation under Mild Conditions. / Organometallics 2004, / 23(12), 3031鈥?036. CrossRef
    58. Henderson, W.; Fawcett, J.; Kemmitt, R. D. W.; McKenna, P.; Russell, D. R. Decomposition Pathways of Platinum(II) Complexes Containing Alkyl and Halide Ligands Investigated by Electrospray Mass Spectrometry. The X-ray Crystal Structure of cis-[PtCl{CH2C(O)CH2Cl} (PPh3)(2)]. / Polyhedron 1997, / 16(14), 2455鈥?463. CrossRef
    59. Garrou, P. E. Transition-Metal-Mediated Phosphorus-Carbon Bond Cleavage and Its Relevance to Homogeneous Catalyst Deactivation. / Chem. Rev. 1985, / 85(3), 171鈥?85. CrossRef
    60. Qian, R.; Liao, Y. X.; Guo, Y. L.; Guo, H. ESI-FTICR-MS Studies on Gas Phase Fragmentation Reactions of ArPd(PPh3)(2)I Complexes. / J. Am. Soc. Mass Spectrom. 2006, / 17(11), 1582鈥?589. CrossRef
    61. Fahey, D. R.; Mahan, J. E. Reversible Oxidative Addition of Triphenylphosphine to Zero-Valent Nickel and Palladium Complexes / J. Am. Chem. Soc. 1976, / 98(15), 4499鈥?503. CrossRef
    62. Goodson, F. E.; Wallow, T. I.; Novak, B. M. Mechanistic Studies on the Aryl-Aryl Interchange Reaction of ArPdL2I (L= Triarylphosphine) Complexes. / J. Am. Chem. Soc. 1997, / 119, 12441鈥?2453. CrossRef
    63. Foa, M.; Cassar, L. Oxidative Addition of Aryl Halides to Tris(triphenylphosphine)nickel(0). / J. Chem. Soc. Dalton Trans. 1975, 2572鈥?576.
    64. Colon, I.; Kelsey, D. R. Coupling of Aryl Chlorides by Nickel and Reducing Metals. / J. Org. Chem. 1986, / 51(14), 2627鈥?637. CrossRef
    65. Percec, V.; Bae, J. Y.; Zhao, M. Y.; Hill, D. H. Aryl Mesylates in Metal-Catalyzed Homocoupling and from Phenols Via Nickel-Catalyzed Homocoupling of Their Mesylates Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates. / J. Org. Chem. 1995, / 60(1), 176鈥?85. CrossRef
    66. Roithov谩, J.; Schr枚der, D. Gas-Phase Study on the C-C Coupling of Naphthol Catalyzed by CuII. TMEDA: Evidence for the Key Role of Binuclear Clusters. / Chem. Eur. J. 2008, / 14, 2180鈥?188. CrossRef
    67. Hong, R. PhD thesis, Shanghai Inst. of Org. Chem. Chinese. Acad. Sci. 2001, 43鈥?4.
  • 作者单位:Jing Zhou (1)
    Qian Zhao (2)
    Wen-Wen Chen (2)
    Haoyang Wang (1)
    Guo-Qiang Lin (2)
    Ming-Hua Xu (2)
    Yinlong Guo (1)

    1. Shanghai Mass Spectrometry Center, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032, Shanghai, China
    2. CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032, Shanghai, China
文摘
Gas-phase cyclometalation of [ArNi(PPh3)n]+ (n = 1, 2) complexes have been studied by ESI-MS/MS. The electron-donating substituents of aromatic iodides in the para position were found to inhibit the cyclometalation process of losing ArH, while the electron-withdrawing substituents in the para position were found to enhance it. These results indicate that the cyclometalation process of losing ArH is favored by electron-deficient aromatic groups. In addition, the detailed dissociation pathways of the cationic nickel complexes were studied, and among these pathways, the process of aryl-aryl interchange was also found to proceed in ESI-MS/MS.

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