Intramolecular scrambling of aryl groups in organopalladium complexes [ArPd(PPh3)2]+: From solution to the Gas phase, back again, and in-between

Chemistry - An Asian Journal

Volumn 5, Issue 7, 2010, Pages 1667-1676

  Agrawal, Divya ^a   Zins, Emilie Laure ^a   Schröder, Detlef ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Electrospray ionization; Intramolecular scrambling; Palladium catalysts; Phosphine ligands; Solution chemistry

Indexed keywords

ARYL GROUP; CONDENSED PHASE; ESI MASS SPECTROMETRY; FRAGMENT IONS; FRAGMENTATION PATHWAYS; GASPHASE; IN-BETWEEN; ORGANOPALLADIUM COMPLEXES; PALLADIUM CATALYST; PARENT IONS; PHENYL GROUP; PHOSPHINE LIGANDS; SOLUTION CHEMISTRY; STATISTICAL MODELS; TANDEM MASS SPECTROMETRIC;

CATALYSTS; DEUTERIUM; GASES; IONIZATION OF GASES; LIGANDS; MASS SPECTROMETRY; PALLADIUM; PALLADIUM COMPOUNDS; PARTICLE DETECTORS; PHOSPHORUS; PHOSPHORUS COMPOUNDS;

ELECTROSPRAY IONIZATION;

EID: 77954358773     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000086     Document Type: Article

References (100)

1. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
2. W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2-7.
3. J. Tsuji, T. Mandai, Angew. Chem. 1995, 107, 2830-2854;
4. Angew. Chem. Int. Ed. Engl. 1995, 34, 2589-2612.
5. J. P. Wolfe, S. Wagaw, J. F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805-818.
6. S. P. Stanforth, Tetrahedron 1998, 54, 263-303.
7. J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177;
8. Angew. Chem. Int. Ed. 1998, 37, 2046-2067.
9. a) K.-C. Kong, C.-H. Cheng, J. Am. Chem. Soc. 1991, 113, 6313-6315;
10. W. A. Herrmann, C. Brossmer, T. Priermeier, K. Öfele, J. Organomet. Chem. 1994, 481, 97-108;
11. B. E. Segelstein, T. W. Butler, B. L. Chenard, J. Org. Chem. 1995, 60, 12-13;
12. M. Sakamoto, I. Shimizu, A. Yamamoto, Chem. Lett. 1995, 1101-1102;
13. F. E. Goodson, T. I. Wallow, B. M. Novak, J. Am. Chem. Soc. 1997, 119, 12441-12453;
14. J. P. Flemming, M. C. Pilon, O. Y. Borbulevitch, M. Y. Antipin, V. V. Grushin, Inorg. Chim. Acta 1998, 280, 87-98;
15. V. V. Grushin, Organometallics 2000, 19, 1888-1900.
16. D. K. Morita, J. K. Stille, J. R. Norton, J. Am. Chem. Soc. 1995, 117, 8576-8581.
17. a) D. F. O'Keefe, M. C. Dannock, S. M. Marcuccio, Tetrahedron Lett. 1992, 33, 6679-6680;
18. W. A. Herrmann, C. Brossmer, K. Öfele, M. Beller, H. Fischer, J. Mol. Catal. A 1995, 103, 133-146;
19. W. A. Herrmann, C. Brossmer, K. Öfele, M. Beller, H. Fischer, J. Organomet. Chem. 1995, 491, C1-C4.
20. a) V. V. Grushin, C. Bensimon, H. Alper, Organometallics 1995, 14, 3259-3263;
21. D. Barañano, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 2937-2938;
22. M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 4708-4709.
23. a) B. M. Trost, J.-P. Surivet, J. Am. Chem. Soc. 2000, 122, 6291-6292;
24. B. M. Trost, J.-P. Surivet, Angew. Chem. 2000, 112, 3252-3254;
25. Angew. Chem. Int. Ed. 2000, 39, 3122-3124;
26. B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599-1626;
27. C. C. Mauger, G. A. Mignani, Aldrichimica Acta 2006, 39, 17-24;
28. R. A. Altman, S. L. Buchwald, Org. Lett. 2006, 8, 2779-2782;
29. A. Shafir, S. L. Buchwald, J. Am. Chem. Soc. 2006, 128, 8742-8743;
30. K. Billingsley, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3358-3366.
31. a) J. V. Ortiz, Z. Havlas, R. Hoffman, Helv. Chim. Acta 1984, 67, 1-17;
32. P. E. Garrou, Chem. Rev. 1985, 85, 171-185;
33. H. Nakazawa, Y. Matsuoka, I. Nakagawa, K. Miyoshi, Organometallics 1992, 11, 1385-1392;
34. M. T. Reetz, G. Lohmer, R. Schwickardi, Angew. Chem. 1998, 110, 492-495;
35. Angew. Chem. Int. Ed. 1998, 37, 481-483;
36. L. K. Hwang, Y. Na, J. Lee, Y. Do, S. Chang, Angew. Chem. 2005, 117, 6322-6325;
37. Angew. Chem. Int. Ed. 2005, 44, 6166-6169.
38. a) R. Qian, Y.-X. Liao, Y.-L. Guo, H. Guo, J. Am. Soc. Mass Spectrom. J. Am. Soc. Mass. Spectrom. 2006, 17, 1582-1589;
39. R. Qian, H. Guo, Y. Liao, H. Wang, X. Zhang, Y. Guo, Rapid Commun. Mass Spectrom. 2006, 20, 589-594.
40. a) G. Bracher, B. Kellenberger, L. M. Venanzi, Helv. Chim. Acta 1988, 71, 1442-1457;
41. L. S. Sunderlin, R. R. Squires, J. Am. Chem. Soc. 1993, 115, 337-343;
42. A. O. Aliprantis, J. W. Canary, J. Am. Chem. Soc. 1994, 116, 6985-6986;
43. C. Adlhart, C. Hinderling, H. Baumann, P. Chen, J. Am. Chem. Soc. 2000, 122, 8204-8214;
44. R. A. J. O'Hair, A. K. Vrkic, P. F. James, J. Am. Chem. Soc. 2004, 126, 12173-12 183;
45. P. F. James, R. A. J. OáHair, Org. Lett. 2004, 6, 2761-2764;
46. G. Bhaskar, M. A. Chary, M. K. Kumar, K. Syamasundar, M. Vair-amani, S. Prabhaker, Rapid Commun. Mass Spectrom. 2005, 19, 1536-1544;
47. M. Schlangen, J. Neugebauer, M. Reiher, D. Schröder, J. Pitarch López, M. Haryono, F. W. Heinemann, A. Grohmann, H. Schwarz, J. Am. Chem. Soc. 2008, 130, 4285-4294.
48. a) R. Colton, A. D'Agostino, J. C. Traeger, Mass Spectrom. Rev. 1995, 14, 79-106;
49. W. Henderson, B. K. Nicholson, L. J. McCaffrey, Polyhedron 1998, 17, 4291-4313;
50. J. C. Traeger, Int. J. Mass Spectrom. 2000, 200, 387-401;
51. A. Roglans, A. Pla-Quintana, Palladium Intermediates in Solution in Reactive Intermediates: MS Investigations in Solution (Ed.: L. S. Santos), Wiley-VCH, Weinheim, 2010.
52. a) A. R. Dick, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 12790-12791;
53. M. P. Lanci, M. S. Remy, W. Kaminsky, J. M. Mayer, M. S. Sanford, J. Am. Chem. Soc. 2009, 131, 15618-15620;
54. T. W. Lyons, M. S. Sanford, Tetrahedron 2009, 65, 3211-3221;
55. G. L. Hamilton, F. D. Toste, Nature 2009, 459, 917-918.
56. Neutralization-reionization mass spectrometry has been used to characterize the organic products formed in metal-mediated reactions in the gas phase, see:a) D. Schröder, D. Sülzle, J. Hrušák, D. K. Böhme, H. Schwarz, Int. J. Mass Spectrom. Ion Processes 1991, 110, 145-156;
57. D. Schröder, H. Schwarz, Helv. Chim. Acta 1992, 75, 1281-1287;
58. D. Schröder, J. Müller, H. Schwarz, Organometallics 1993, 12, 1972-1975;
59. D. Schröder, H. Schwarz, S. Polarz, M. Driess, Phys. Chem. Chem. Phys. 2005, 7, 1049-1053.
60. a) J. Roithová, D. Schröder, Chem. Eur. J. 2008, 14, 2180-2188;
61. J. Šrogl, J. Hyvl, A. R v sz, D. Schröder, Chem. Commun. 2009, 3463-3465;
62. J. Roithová, P. Milko, J. Am. Chem. Soc. 2010, 132, 281-288.
63. a) N. G. Tsierkezos, J. Roithová, D. Schröder, I. E. Molinou, H. Schwarz, J. Phys. Chem. B 2008, 112, 4365-4371;
64. J. Míšek, M. Tichý, I. G. Stará, I. Starý, D. Schröder, Collect. Czech Chem. Commun. 2009, 74, 323-333;
65. N. G. Tsierkezos, J. Roithová, D. Schröder, M. Ončák, P. Slavíček, Inorg. Chem. 2009, 48, 6287-6296.
66. D. Schröder, K. P. de Jong, J. Roithová, Eur. J. Inorg. Chem. 2009, 2121-2128.
67. N. B. Cech, C. G. Enke, Mass Spectrom. Rev. 2001, 20, 362-387.
68. E.-L. Zins, C. Pepe, D. Schröder, Faraday Discuss. 2010, 145, 157-169.
69. Although these sequential ion-molecule reactions occurring during ion storage are a drawback of ion-trap experiments, which complicates the analysis of the data, they do not affect the conclusions derived from the experiments. For similar examples, see:a) B. Jagoda-Cwiklik, P. Jungwirth, L. Rulíšek, P. Milko, J. Roithová, J. Lemaire, P. Maitre, J. M. Ortega, D. Schröder, Chem Phys Chem 2007, 8, 1629-1639;
70. P. Milko, J. Roithová, D. Schröder, J. Lemaire, H. Schwarz, M. C. Holthausen, Chem. Eur. J. 2008, 14, 4318-4327;
71. E. C. Tyo, A. W. Castleman Jr., D. Schröder, P. Milko, J. Roithová, J. M. Ortega, M. A. Cinellu, F. Cocco, G. Minghetti, J. Am. Chem. Soc. 2009, 131, 13009-13019.
72. a) Á. Révész, P. Milko, J. Z. abka, D. Schröder, J. Roithová, J. Mass Spectrom., unpublished results;
73. E. L. Zins, C. Pepe, D. Schröder, J. Mass Spectrom., unpublished results.
74. For a recent review of C-H bond activation in the gas phase, see: J. Roithová, D. Schröder, Chem. Rev. 2010, 110, 1170-1211.
75. a) J. Loos, D. Schröder, W. Zummack, H. Schwarz, R. Thissen, O. Dutuit, Int. J. Mass Spectrom. 2002, 214, 105-128;
76. C. Trage, D. Schröder, H. Schwarz, Organometallics 2003, 22, 693-707
77. (addendum: C. Trage, D. Schröder, H. Schwarz, Organometallics 2003, 22, 1348-1348);
78. M. Schlangen, D. Schröder, H. Schwarz, Helv. Chim. Acta 2005, 88, 1405-1420;
79. B. Butschke, M. Schlangen, H. Schwarz, D. Schröder, Z. Naturf. B 2007, 62 b, 309-313;
80. B. Butschke, D. Schröder, H. Schwarz, Organometallics 2009, 28, 4340-4349.
81. 35 (24 %).a) D. Schröder, H. Schwarz, S. Schenk, E. Anders, Angew. Chem. 2003, 115, 5241-5244;
82. Angew. Chem. Int. Ed. 2003, 42, 5087-5090;
83. Angew. Chem. Int. Ed. 2003, 42, 5087-5090;
84. J. Míšek, M. Tichý, I. G. Stará, I. Starý, J. Roithová, D. Schröder, Croat. Chem. Acta 2009, 82, 79-86.
85. a) K. Kikukawa, T. Yamane, M. Takagi, T. Matsuda, J. Chem. Soc. Chem. Commun. 1972, 695-696;
86. T. Yamane, K. Kikukawa, M. Takagi, T. Matsuda, Tetrahedron 1973, 29, 955-962;
87. R. Asano, I. Moritani, Y. Fujiwara, S. Teranishi, Bull. Chem. Soc. Jpn. 1973, 46, 2910-2911;
88. D. R. Fahey, J. E. Mahan, J. Am. Chem. Soc. 1976, 98, 4499-4503;
89. T. Kawamura, K. Kikukawa, M. Takagi, T. Matsuda, Bull. Chem. Soc. Jpn. 1977, 50, 2021-2024;
90. K. Kikukawa, T. Yamane, Y. Ohbe, M. Takagi, T. Matsuda, Bull. Chem. Soc. Jpn. 1979, 52, 1187-1190;
91. K. Kikukawa, M. Takagi, T. Matsuda, Bull. Chem. Soc. Jpn. 1979, 52, 1493-1497.
92. P. Fitton, M. P. Johnson, J. E. McKeon, J. Chem. Soc. Chem. Commun. 1968, 6-9.
93. a) E. G. Samsel, J. R. Norton, J. Am. Chem. Soc. 1984, 106, 5505-5512;
94. J. R. Brumbaugh, R. R. Whittle, M. Parvez, A. Sen, Organometallics 1990, 9, 1735-1747;
95. F. Ozawa, A. Kubo, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 1417-1419.
96. A. Tintaru, J. Roithová, D. Schröder, L. Charles, I. Jus.inski, Z. Glasovac, M. Eckert-Maksić, J. Phys. Chem. A 2008, 112, 12097-12103.
97. T. Aggerholm, S. C. Nanita, K. J. Koch, R. G. Cooks, J. Mass Spectrom. 2003, 38, 87-97.
98. R. A. J. O'Hair, A. K. Vrkic, P. F. James, J. Am. Chem. Soc. 2004, 126, 12173-12183.
99. For first applications of this conversion Scheme to the CID of other gaseous ions in ion-trap mass spectrometry, see:a) N. G. Tsierkezos, M. Buchta, P. Holý, D. Schröder, Rapid Commun. Mass Spectrom. 2009, 23, 1550-1556;
100. D. Schröder, L. Ducháčková, I. Jušinski, M. Eckert-Maksić, J. Heyda, L. Tůma, P. Jungwirth, Chem. Phys. Lett. 2010, 490, 14-18.