Unimolecular reactions of organocuprates and organoargentates

Organometallics

Volumn 29, Issue 10, 2010, Pages 2282-2291

  Rijs, Nicole J ^a   O'Hair, Richard A J ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BOND ENERGIES; COLLISION-INDUCED DISSOCIATION; DENSITY FUNCTIONAL THEORY CALCULATIONS; DEUTERIUM LABELING; DFT CALCULATION; GAS-PHASE FRAGMENTATION; GASPHASE; HOMOLYSIS; ORBITALS; UNIMOLECULAR REACTIONS;

CHEMICAL BONDS; CHEMICAL REACTIONS; DEUTERIUM; SILVER;

DENSITY FUNCTIONAL THEORY;

EID: 77955186526     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1000875     Document Type: Article

References (116)

1. (a) Modern Organocopper Chemistry, Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
2. (b) Lipsliutz, B. H. Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, U.K., 1994; pp 283-382.
3. (c) Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, U.K., 1994.
4. For X = C see: (a) Halbes-Letinois, U.; Weibel. J.-M.: Pale, P. Chem. Soc. Rev. 2007, 36, 759.
5. (b) Power, R. H.; Williams, C. M.; Raine, A. L.; Harper, J. B. Org. Lett. 2005, 7, 1323.
6. (c) Pouwer, R. H.; Harper, J. B.; Vyakaranam, K.; Michl, J.; Williams, C. M.; Jessen, C. H.; Bernhardt, P. V. Eur. J Org. Chem. 2007, 2, 241.
7. (d) Someyaa, H.; Yorimitsu, H.; Oshima, K. Tetrahedron Lett. 2009, 50, 3270. For X = Si see:
8. (e) Murakami, K.; Hirano, K.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2008, 47, 5833.
9. For an entire issue of Chemical Reviews devoted to the theme of coinage metals in organic synthesis see: Chem. Rev. 2008, 108, issue 8, Lipshutz, B. H., Yamamoto, Y. Eds.
10. (a) Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, U.K., 1994; pp 60-61. Fast decomposition of n-propylsilver (I) occurs at -60 °C:
11. (b) Westmijze, H.; Kleijn, H.; Vermeer, P. J. Organomet. Chem. 1979, 172, 377.
12. For reviews and key references on the general mechanistic features of decomposition reactions of organometallics see:
13. (a) Baird, M. C. J Organomet. Chem. 1974, 64, 289.
14. (b) Davidson, P. J.; Lappert, M. F.; Pearce, R. Chem. Rev. 1976, 76, 219.
15. (c) Akermark, B.; Ljungqvist, A. J. Organomet. Chem. 1979, 182, 59.
16. (d) Barker, P. J.; Winter, J. N. in The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: Chichester, U.K., 1985; Vol. 2, Chapter 3.
17. (e) Hager, E.; Sivaramakrishna, A.; Clayton, H. S.; Mogorosi, M. M.; Moss, J. R. Coord. Chem. Rev. 2008, 252, 1668.
18. (a) Whitesides, G. M.; Stedronsky, E. R.; Casey, C. P.; San Filippo, J. J. Am. Chem. Soc. 1970, 92, 1426.
19. (b) Whitesides, G. M.; Bergbreiter, D. E.; Kendall, P. F, J. Am. Chem. Soc. 1974, 96, 2806.
20. (c) Miyashita, A.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1977, 50, 1109.
21. (d) House, H. O.; DuBose, J. C. J. Org. Chem. 1975, 40, 788.
22. (a) Whitesides, G. M.; Panek, E. J.; Stedronsky, E. R. J. Am. Chem. Soc. 1972, 94, 232.
23. (b) Hashimoto, H.; Nakano, T. J. Org. Chem. 1966, 31, 891.
24. (c) Bergbreiter, D. E.; Lynch, T. J. J. Org. Chem. 1981, 46, 727.
25. (d) Yamamoto, K.; Nakanishi, K.; Kumada, M. J. Organomet. Chem. 1967, 7, 197.
26. (e) Shutova, T. G.; Butovskaya, G. V.; Agabekov, V. E.; Moiseichuk, K. L. Kinet. Catal. 1996, 37, 29.
27. (f) Akermark, B.; Ljumgqvist, A. J. Organomet. Chem. 1979. 182. 47.
28. (a) Whitesides, G. M.; Casey, C. P. J. Am Chem, Soc. 1966, 88, 4541.
29. (b) Kaufmann, T.; Sahm, W. Angew. Chem., Int. 1967, 6, 85.
30. (c) Whitesides, G. M.; Casey, C. P.; Krieger, J. K. J. Am. Chem. Soc. 1971, 93, 1379.
31. (d) Pasynkiewicz, S.; Poplawska, J. J. Organomet. Chem. 1985, 282, 427.
32. (e) Pasynkiewicz, S.; Pikul, S.; Poplawska, J. J. Organomet. Chem. 1985, 293, 125.
33. (f) Pasynkiewicz, S.; J. Organomet. Chem. 1990, 387, 1.
34. (g) Akermark, B.; Ljungqvist, A. J. Organomet. Chem. 1979, 182, 47.
35. For examples of reductive elimination reactions of well-detined copper cluster compounds see: (a) Cairncross, A.; Sheppard, W. A. J. Am. Chem. Soc. 1971, 93, 247.
36. (b) van Koten, G.; Noltes, J. G. J. Chem, Soc., Chem. Commun. 1974, 575.
37. (c) Cohen, T.; Treblow, M. D. J. Org. Chem. 1976. 41. 1986.
38. (d) Janssen, M. D.; Corsten, M. A.; Spek, A. L.; Grove, D. M.; van Koten, G. Orgnometallics 1996, 15, 2810.
39. (a) Wiemers, D. M.; Burton, D. J. J. Am. Chem, Soc. 1986, 108, 832-4.
40. (b) Yang, Z. Y.; Wiemers, D. M.; Burton, D. J. J. Am. Chem. SOc. 1992, 114, 4402-3.
41. (c) Yang, Z.-Y.; Burton, D. J. J. Fluorine Chem. 2000, 102, 89-103.
42. (a) Wada, K.; Tamura, M.; Kochi, J. J. Am. Chem., Soc. 1970, 92, 6656.
43. (b) Kochi, J. Acc. Chem. Res. 1974, 7, 351.
44. (c) Tamura, M.; Kochi, J. K. Bull, Chem. Soc. Jon. 1972, 45, 1120.
45. The nature of both the organic ligand. and the coligand can have a profound effect on the thermal stability of organocuprates: (a) van Koten, G.; James, S. L.; Jastrzebski, J. T. B. H. Comprehensive Organometallic Chemistry II; Pergamon Press: Oxford, U.K., 1995; Vol. 5, pp 75-77.
46. (b) Bertz, S. H.; Dabbagh,G. J. Chem. Soc. Chem. Commun. 1982, 1030.
47. Surry, D. S.; Spring, D. R. Chem. Soc. Rev. 2006, 35, 218.
48. (a) Kocienski, P.; Barber, C. Pure Appl. Chem. 1990, 62, 1933.
49. (b) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. J. Am. Chem, Soc. 2001, 123, 11109.
50. (c) Kondo, J.; Iio, Y.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 106-108.
51. (d) Kondo, J.; Someya, H.; Kinoshita, H.; Shinokubo, H.; Yorimitsu, H.; Oshima, K. Org. Lett. 2005, 7, 5713-5715.
52. For a review on gas-phase metal cluster ion chemistry see: O'Hair, R. A. J.; Khairallah, G. N. J. Cluster Sci. 2004, 15, 331.
53. nAg]+, see: Wang, F. Q.; Khairallah, G. N.; Koutsantonis. G. A.; Williams, C. M.; Callahan, D. L.; O'Hair, R. A. J. Phys, Chem. Chem. 2009, 11, 4132-4135.
54. O'Hair, R. A. J. Chem. Commun. 2006, 1469.
55. For reviews of DFT methods to calculate potential energy surfaces for organometallic reactions see: (a) Ziegler, T.; Autschbach, J. Chem Rev. 2005, 105, 2695-2722.
56. (b) Niu, S.; Hall, M. B. Chem, Rev. 2000, 100, 353-406.
57. For a review on the marriage of theory and experiment for coinage metal ions see: Roithová, J.; Schröder, D. Coord, Chem, Rev. 2009, 253, 666.
58. O'Hair, R. A. J. Gas Phase Ligand Fragmentation to Unmask Reactive Metallic Species. In MS Investigations of Reactive Intermediates in Solution: Santos, L. S., Ed.; Wiley-VCH: Weinheim, Germany, 2010; Chapter 6, pp 199-227 (ISBN: 978-3-527-32351-7).
59. For examples on the direct use of ESI/MS on solutions of organometallates see: (a) Lipshutz, B. H.; Keith, J.; Buzard, D. JOrganometallics 1999, 18, 1571.
60. (b) Koszinowski, K.; Boehrer, P. Organometallics 2009, 25, 100.
61. (c) Koszinowski, K.; Boehrer, P. Organometallics 2009, 25, 771.
62. (a) O'Hair, R. A. J. Chem. Commun. 2002, 20.
63. (b) O'Hair, R. A. J.; Vrkic, A. K.; James, P. F. J. Am, Chem. Soc. 2004, 126, 12173.
64. (c) James, P. F.; O'Hair, R. A. J. Org. Lett. 2004, 6, 2761.
65. (d) Jacob, A. P.; James, P. F.; O'Hair, R. A. J. Int. J. Mass Spectrom. 2006, 255-256, 45.
66. (e) O'Hair, R. A. J.; Waters, T.; Cao, B. Angew, Chem., Int. Ed. 2007, 46, 7048.
67. (f) Rijs, N.; Waters, T.; Khairallah, G. N.; O'Hair, R. A. J. J. Am. Chem. Sac 2008, 130, 1069.
68. (g) Thum, C. C. L.; Khairallah, G. N.; O'Hair, R. A. J. Angew, Chem., Int. Ed. 2008, 47, 9118.
69. (h) Khairallah, G. N.; Waters, T.; O'Hair, R. A. JDalton Trans. 2009, 2832-2836.
70. (i) Rijs, N. J.; O'Hair, R. A. J. Organometallics 2009, 25, 2684-2692.
71. (j) Khairallah, G. N.; Thum, C.; O'Hair, R. A. JOrganometallics 2009, 28, 5002-5011.
72. (k) Rijs, N. J.; Yates, B. F.; O'Hair, R. A. J. Chem. Eur. J. 2010, 16, 2674-2678.
73. Khairallah, G. N.; Yoo, E. J. H.; O'Hair, R. A. J, Organometallics 2010, 29, 1238-1245.
74. For older reviews focusing on the condensed-phase formation of organometallics via decarboxylation reactions see: (a) Deacon, G. B. Organomet. Chem. Rev. A 1970, 5, 355.
75. (b) Deacon, G. B.; Faulks, S. J.; Pain, G. N. Adv. Organomet. Chem. 1986, 25, 237.
76. For recent reviews on metal-catalyzed, transformations of carboxylic acids see: (a) Goossen, L. J.; Goossen, K.; Rodriguez, N.; Blanchot, M.; Linder, C.; Zimmermann, B. Pure Appl. Chem. 2008, 80, 1725.
77. (b) Goossen, L. J.; Rodriguez, N.; Goossen, K. Angew. Chem., Int. Ed. 2008, 47, 3100.
78. Copper and silver carboxylates are also used in solution as precursors for generation of reactive organometallic species in catalytic applications. For recent examples see: (a) Yin, L.; Kanai, M.; Shibasaki, M. J. Am, Chem. Soc. 2009, 131, 9610.
79. (b) Lu, P. F.; Sanchez, C.; Cornella, J.; Larrosa, I. Org. Lett. 2009, 11, 5710.
80. (c) Goossen, L. J.; Linder, C.; Rodriguez, N.; Lange, P. P.; Fromm, A. Chem. Commun. 2009, 7173.
81. (d) Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H. Z.; Liu, L. Angew. Chem., Int Ed. 2009, 48, 9350.
82. For reviews on dyotropic rearrangements see: (a) Reetz, M. T. Adv. Organomet. Chem.1977, 16, 33.
83. (b) Fernandez, I.; Cossio, F. P.; Sierra, M. A. Chem. Rev. 2009, 109, 6687.
84. (c) Gridnev, I. D. Coord. Chem. Rev. 2008, 252, 1798.
85. (a) Lipshutz, B. H. Svnlett 2009, 04, 509.
86. (b) Deutsch, C.; Lipshutz, B. H.; Krause, N. Org. Lett. 2009, 11, 5010.
87. (c) Pelss, A.; Kumpulainen, E. T. T.; Koskinen, A. M. P. J. Org. Chem. 2009, 74, 7598.
88. Frisch, M. J. et al. Gaussian 03; Gaussian, Inc., Pittsburgh, PA, 2003.
89. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
90. (b) Lee, C.; Yang, W.; Parr, R. G. Phys, Rey. B. 1988, 37, 785.
91. (a) Dolg, M.; Wedig, U.; Stoll, H.; Preuss, H. J. Chem. Phys. 1987, 86, 866.
92. (b) Hariharan, P. C.; Pople, J. A. Theor, Chim. Acta 1973, 28, 213.
93. (c) Clark, T.; Chandrasekhar, J.; Schleyer, P. v. R. J. Comput, Chem. 1983, 4, 294.
94. (d) Krishnam, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
95. (e) Gill, P. M. W.; Johnson, B. G.; Pople, J. A.; Frisch, M. J. Chem, Phys. Lett. 1992, 197, 499.
96. For the structure of the simplest model system, the dimethylcuprate ion [MeCuMe]-. see: (a) Hope. H.: Olmstead. M. M.; Power, P. P.; Sandell, J.; Xu, X. J. Am. Chem. Soc.1985, 107, 4337.
97. (b) Dempsey, D. F.; Girolami, G. S. Organametallics 1988, 7, 1208.
98. Grotiahn. D. B.; Halfen. D. T.: Ziurys. L. M.; Cooksy, A. L. J. Am. Chem. Sac. 2004, 126, 12621-12627.
99. 2]-. See:
100. (a) Andrews, L.; Wang, X. J. Am. Chem. Soc. 2003, 125, 11759.
101. (b) Wang, X.; Andrews, L. Angew. Chem., Int Ed. 2003, 42, 5201.
102. Calo(CuCN) = 1.58 eV. Experimental data are taken from: (a) Calvi. R. M. D.: Andrews, D. H.; Lineberger, W. C. Chem. Phys. Lett. 2007, 442, 12-16.
103. (b) Yuichi, N.; Tomokazu, Y.; Fumitaka, H.; Miki, K.; Satoshi, Y.; Atsushi, N.; Koji, K. J. Chem. Phys. 2000, 113, 1725-1731.
104. (a) Feng, Y.; Liu, L.; Wang, J. T.; Huang, H.; Guo, Q. X. J. Chem. Int. Comvut, Sci. 2003, 43, 2005.
105. (b) Rijs, N. J; Brookes, N. J.; O'Hair, R. A. J.; Yates, B. F., Manuscript in preparation.
106. For a review on the isotope effects associated with the formation and reactions of metal hydrides see: Bullock, R. M. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992; Chapter 8.
107. 2, since it is not observed experimentally.
108. Some related coinage metal radical anions, [RM]-, have been previously observed experimentally and/or studied via theory: for R = Ph and M = Cu, Ag, see: (a) Liu, X.-J.; Zhang, X.; Han, K.-L.; Xing, X.-P.; Sun, S.-T.; Tang, Z.-C. J. Phys. Chem. A 2007, 111, 3248-3255.
109. (b) Liu, X.-J.; Yang, C.-L.; Zhang, X.; Han, K.-L.; Tang, Z.-C. J. Comput. Chem. 2008, 29, 1674-1667.
110. For R - CN and M - Cu, Ag, see: (c) Boldyrev, A. I.; Li, X.; Wang, L.-S. J. Chem, Phys. 2000, 112, 3627-3632.
111. Gas-phase thermochemical data and definitions (e.g., anion proton affinity) are taken from the NIST Web site: http://webbook. nist.gov/chemistry/
112. (a) Mori, S.; Nakamura, E. J. Mol Struct (THEOCHEM) 1999, 461, 167-175.
113. (b) Nakanishi, W.; Yamanaka, M.; Nakamura, E. J. Am. Chem. Soc. 2005, 127, 1446.
114. •- in detail.
115. Indeed, Pd-catalyzed C-C bond coupling of acetylide ligands formed by decarboxylation has been recently described: (a) Rayabarapu, D. K.; Tunge, J. A. J. Am. Chem. Soc. 2005, 127, 13510.
116. (b) Kolarovic, A.; Fáberová, Z. J. Org. 2009, 74, 7199.