Thermal (iodide) and photoinduced electron-transfer catalysis in biaryl synthesis via aromatic arylations with diazonium salts

Journal of the American Chemical Society

Volumn 119, Issue 21, 1997, Pages 4846-4855

  Kosynkin, D ^a   Bockman, T M ^a   Kochi, J K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON; DIAZONIUM COMPOUND; IODIDE; PENTAFLUOROBENZENEDIAZONIUM FLUOROBORATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; ELECTRON TRANSPORT;

EID: 0031007139     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970599b     Document Type: Article

References (95)

1. (a) Wulfman, D. E. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: New York, 1978; p 290. See also the other chapters dealing with diazonium decompositions.
2. (b) Zollinger, H. Diazo Chemistry; VCH: New York, 1994; Vol. 1.
3. Galli, C. Chem. Rev. 1988, 88, 765.
4. (a) Lewin, A. H.; Cohen, T. J. Org. Chem. 1967, 32, 3844.
5. (b) Lewis, E. S.; Johnson, M. D. J. Am. Chem. Soc. 1959, 81, 2070.
6. (c) Waters, W. A. J. Chem. Soc. 1942, 266.
7. (a) Cowdrey, W. A.; Davies, D. S. Chem. Soc. Quart. Rev. 1952, 6, 358.
8. (b) Cohen, T.; Lewarchik, R. J.; Tarino, J. Z. J. Am. Chem. Soc. 1974, 96, 7753.
9. (a) Rondestvedt, C. S. Org. React. 1960, 11, 189.
10. (b) Kochi, J. K. J. Am. Chem. Soc. 1957, 79, 2942.
11. (a) Beadle, J. R.; Korzeniowski, S. H.; Rosenberg, D. E.; Garcia-Slanga, B. J.; Gokel, G. W. J. Org. Chem. 1984, 49, 1594.
12. (b) Rüchardt, C.; Merz, E.; Freudenberg, B.; Opgenorth, H.-J.; Tan, C. C.; Werner, R. Essays on Free-Radical Chemistry; Special Publication No. 24, Norman, R. O. C., Ed.; Chemical Society London: London, 1970; p 51ff and references therein.
13. (a) Gomberg, M.; Bachmann, W. E. J. Am. Chem. Soc. 1924, 46, 2339.
14. (b) Bachmann, W. E.; Hoffman, R. A. Org. React. 1944, 2, 224.
15. (c) DeTar, D. F. Org. React. 1957, 9, 409.
16. (a) Pschorr, R. Chem. Ber. 1896, 29, 496.
17. (b) Abramovitch, R. A. Adv. Free Radical Chem. 1966, 2, 4787.
18. Dreher, E.; Niederer, P.; Schwarz, W.; Zollinger, H. Helv. Chim Acta 1981, 64, 488.
19. See, e.g.: (a) Marder, S. R.; Sohn, J. E.; Stucky, G. D. Materials for Nonlinear Optics: Chemical Perspectives: American Chemical Society: Washington, DC, 1991. (b) Okada, M.; Shiuchi, K.; Funada, F.; Numada, H.; Ichinose, H.; Sasake, K.; Plach, H.; Poetsch, E. German Patent 4,426,904; 4,426,905 [Chem. Abstr. 122, 27861, 278762].
20. See, e.g.: (a) Marder, S. R.; Sohn, J. E.; Stucky, G. D. Materials for Nonlinear Optics: Chemical Perspectives: American Chemical Society: Washington, DC, 1991. (b) Okada, M.; Shiuchi, K.; Funada, F.; Numada, H.; Ichinose, H.; Sasake, K.; Plach, H.; Poetsch, E. German Patent 4,426,904; 4,426,905 [Chem. Abstr. 122, 27861, 278762].
21. (a) Treatment of I with excess HCl in nitromethane at 25°C affords crystalline 2,4,6-trichloro-3,5-difluorobenzenediazonium hexafluorophosphate in 80% yield.
22. (b) Bockman, T. M.; Kosynkin, D.; Kochi, J. K. To be submitted for publication.
23. Kampar, V. E.; Kokars, V. R.; Neiland, O. Ya. Zh. Obs. Khim. (Engl. Transl.) 1977, 47, 858. See also: Koller, S.; Zollinger, H. Helv. Chim. Acta 1970, 53, 78.
24. Kampar, V. E.; Kokars, V. R.; Neiland, O. Ya. Zh. Obs. Khim. (Engl. Transl.) 1977, 47, 858. See also: Koller, S.; Zollinger, H. Helv. Chim. Acta 1970, 53, 78.
25. (a) Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 811. See also: Foster, R. F. Organic Charge-Transfer Complexes: Academic: New York, 1965. Briegleb, G. Elektronen Donator-Acceptor Komplexe; Springer: Berlin, 1961.
26. (a) Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 811. See also: Foster, R. F. Organic Charge-Transfer Complexes: Academic: New York, 1965. Briegleb, G. Elektronen Donator-Acceptor Komplexe; Springer: Berlin, 1961.
27. (a) Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 811. See also: Foster, R. F. Organic Charge-Transfer Complexes: Academic: New York, 1965. Briegleb, G. Elektronen Donator-Acceptor Komplexe; Springer: Berlin, 1961.
28. (b) This charge-transfer formulation is now confirmed by the isolation and X-ray crystallography of various types of intermolecular complexes in eq 3 (to be submitted for publication).
29. Compare: Kochi, J. K. Pure. Appl. Chem. 1991, 63, 255.
30. (a) Abeywickrema, A. N.; Beckwith, A. L. J. J. Org. Chem. 1987, 52, 2768.
31. (b) Carey, J. G.; Jones, G.; Millar, I. T. Chem. Ind. 1959, 1018.
32. (c) Carey, J. G.; Millar, I. T. Chem. Ind. 1960, 97.
33. 11b
34. Gritzner, G.; Kuta, J. Pure Appl. Chem. 1984, 56, 461.
35. Rathore, R.; Bosch, E.; Kochi, J. K. Tetrahedron 1994, 23, 6727.
36. Margaretha, P.; Tissot, P. Org. Synth. 1977, 57, 92.
37. (a) Birks, J. B. Photophysics of Aromatic Molecules; Wiley: New York, 1970, p 457ff.
38. (b) Bock, H.; Wagner, G. Tetrahedron Lett. 1971, 3713.
39. Tsubomura, H.; Mulliken, R. S. J. Am. Chem. Soc. 1960, 82, 5966.
40. exc > 410 nm, the output of a 500-W high-pressure mercury light was successively passed through a Pyrex sharp cutoff filter (Corning CS 3-74) and a IR water filter.
41. + for quantitative photochemical studies.
42. Hatchard, C. G.; Parker, C. A. Proc. R. Soc. 1956, 253, 518.
43. The output of a 450-W Xenon lamp was passed through an interference filter (Oriel 53810) with bandwidth (fwhm) ±10 nm.
44. + cannot be the common precursor since it does not directly react (thermally) with the arenes in Tables 1 and 2.
45. (a) Bolton, R.; Williams, G. H. Adv. Free Radical Chem. 1975, 5, 1.
46. (b) Burdon, J.; Campbell, J. G.; Tatlow, J. C. J. J. Chem. Soc. (C) 1969, 822.
47. (c) Oldham, P. H.; Williams, G. H. J. Chem. Soc. (C) 1970, 1260.
48. (d) Bolton, R.; Coleman, M. W., Williams, G. H. Fluorine Chem. 1974, 4, 363.
49. (e) Bolton, R.; Williams, G. H. Chem. Soc. Rev. 1986, 15, 261.
50. (f) Oldham, P. H.; Williams, G. H.; Wilson, B. A. J. Chem. Soc. (C) 1971, 1094.
51. (a) Frohn, H. J.; Klose, A.; Bardin, V. V. J. Fluorine Chem. 1993, 64, 201.
52. (b) Birchall, J. M.; Haszeldine, R. N.; Wilkinson, M. J. Chem. Soc., Perkin Trans. 1 1974, 1740.
53. (c) Birchall, J. M.; Hazard, R.; Haszeldine, R. N.; Wakalski, W. W. J. Chem. Soc. (C) 1967, 47.
54. 30a
55. See: (a) Singh, P. R.; Kumar, R. Aust. J. Chem. 1972, 25, 2133. (b) Pladziewicz, J. R.; Doyle, M. P. J. Imaging Sci. 1989, 33, 57. (c) Brown, K. C.; Doyle, M. P. J. Org. Chem. 1988, 53, 3255. (d) Andersen, M. L.; Handoo, K. L.; Parker, V. D. Acta Chem. Scand. 1991, 45, 983. (e) Gilbert, B. C.; Hanson, P.; Jones, J. R.; Whitwood, J. C.; Timms, A. W. J. Chem. Soc., Perkin Trans. 2 1992, 629.
56. See: (a) Singh, P. R.; Kumar, R. Aust. J. Chem. 1972, 25, 2133. (b) Pladziewicz, J. R.; Doyle, M. P. J. Imaging Sci. 1989, 33, 57. (c) Brown, K. C.; Doyle, M. P. J. Org. Chem. 1988, 53, 3255. (d) Andersen, M. L.; Handoo, K. L.; Parker, V. D. Acta Chem. Scand. 1991, 45, 983. (e) Gilbert, B. C.; Hanson, P.; Jones, J. R.; Whitwood, J. C.; Timms, A. W. J. Chem. Soc., Perkin Trans. 2 1992, 629.
57. See: (a) Singh, P. R.; Kumar, R. Aust. J. Chem. 1972, 25, 2133. (b) Pladziewicz, J. R.; Doyle, M. P. J. Imaging Sci. 1989, 33, 57. (c) Brown, K. C.; Doyle, M. P. J. Org. Chem. 1988, 53, 3255. (d) Andersen, M. L.; Handoo, K. L.; Parker, V. D. Acta Chem. Scand. 1991, 45, 983. (e) Gilbert, B. C.; Hanson, P.; Jones, J. R.; Whitwood, J. C.; Timms, A. W. J. Chem. Soc., Perkin Trans. 2 1992, 629.
58. See: (a) Singh, P. R.; Kumar, R. Aust. J. Chem. 1972, 25, 2133. (b) Pladziewicz, J. R.; Doyle, M. P. J. Imaging Sci. 1989, 33, 57. (c) Brown, K. C.; Doyle, M. P. J. Org. Chem. 1988, 53, 3255. (d) Andersen, M. L.; Handoo, K. L.; Parker, V. D. Acta Chem. Scand. 1991, 45, 983. (e) Gilbert, B. C.; Hanson, P.; Jones, J. R.; Whitwood, J. C.; Timms, A. W. J. Chem. Soc., Perkin Trans. 2 1992, 629.
59. See: (a) Singh, P. R.; Kumar, R. Aust. J. Chem. 1972, 25, 2133. (b) Pladziewicz, J. R.; Doyle, M. P. J. Imaging Sci. 1989, 33, 57. (c) Brown, K. C.; Doyle, M. P. J. Org. Chem. 1988, 53, 3255. (d) Andersen, M. L.; Handoo, K. L.; Parker, V. D. Acta Chem. Scand. 1991, 45, 983. (e) Gilbert, B. C.; Hanson, P.; Jones, J. R.; Whitwood, J. C.; Timms, A. W. J. Chem. Soc., Perkin Trans. 2 1992, 629.
60. Suehiro, T. Rev. Chem. Intermed. 1988, 10, 101.
61. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
62. DeTar, D. F.; Turetzky, M. N. J. Am. Chem. Soc. 1955, 77, 1745.
63. Ingold, K. U. In Free Radicals; Kochi J. K., Ed; Wiley: New York, 1973; Vol. I, p 37.
64. See: Bolton, R.; Williams, G. H. in ref 27e.
65. Taylor, R. Electrophilic Aromatic Substitution; Wiley: New York, 1990; p 278ff.
66. 1,2 this is the first unequivocal example in which the intermolecular (Gomberg-Bachmann) arylation is shown to proceed via a chain process.
67. We suggest that the iodide-promoted intramolecular Pschorr cyclization also proceeds via an analogous ETC mechanism. Compare: (a) Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 196. (b) Beckwith, A. L. J.; Meijs, G. F. J. Org. Chem. 1987, 52, 1922. (c) Karady, S.; Abramson, N. L.; Dolling, U.-H.; Douglas, A. W.; McManemin, G. J.; Marcune, B. J. Am. Chem. Soc. 1995, 117, 5425.
68. We suggest that the iodide-promoted intramolecular Pschorr cyclization also proceeds via an analogous ETC mechanism. Compare: (a) Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 196. (b) Beckwith, A. L. J.; Meijs, G. F. J. Org. Chem. 1987, 52, 1922. (c) Karady, S.; Abramson, N. L.; Dolling, U.-H.; Douglas, A. W.; McManemin, G. J.; Marcune, B. J. Am. Chem. Soc. 1995, 117, 5425.
69. We suggest that the iodide-promoted intramolecular Pschorr cyclization also proceeds via an analogous ETC mechanism. Compare: (a) Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 196. (b) Beckwith, A. L. J.; Meijs, G. F. J. Org. Chem. 1987, 52, 1922. (c) Karady, S.; Abramson, N. L.; Dolling, U.-H.; Douglas, A. W.; McManemin, G. J.; Marcune, B. J. Am. Chem. Soc. 1995, 117, 5425.
70. (a) Chanon, M.; Tobe, M. L. Angew. Chem., Int. Ed. Engl. 1982, 21, 1.
71. (b) Darchen, A., Mahe, C.; Patin, H. New J. Chem. 1983, 7, 453.
72. (c) Kochi, J. K. J. Organomet. Chem. 1986, 300, 139.
73. (d) Colbran, S. B.; Robinson, B. H.; Simpson, J. Organometallics 1983, 2, 943.
74. 41
75. 1 Mechanism; American Chemical Society: Washington, DC, 1983. (c) Mirafzal, G. A.; Liu, J. P.; Bauld, N. L. J. Am. Chem. Soc. 1993, 115, 6072. (d) Bosch, E.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 1319.
76. 1 Mechanism; American Chemical Society: Washington, DC, 1983. (c) Mirafzal, G. A.; Liu, J. P.; Bauld, N. L. J. Am. Chem. Soc. 1993, 115, 6072. (d) Bosch, E.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 1319.
77. 1 Mechanism; American Chemical Society: Washington, DC, 1983. (c) Mirafzal, G. A.; Liu, J. P.; Bauld, N. L. J. Am. Chem. Soc. 1993, 115, 6072. (d) Bosch, E.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 1319.
78. 1 Mechanism; American Chemical Society: Washington, DC, 1983. (c) Mirafzal, G. A.; Liu, J. P.; Bauld, N. L. J. Am. Chem. Soc. 1993, 115, 6072. (d) Bosch, E.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 1319.
79. (a) Weigert, F. J. Comput. Chem. 1987, 11, 273.
80. (b) The program is available from Project Seraphim, 1101 University Ave., Madison, WI 53706.
81. +) as an intermediate in the GEAR simulations of Schemes 1-3 does not alter the predicted yields of either Ar-Ar′ or ArI (see the Experimental Section).
82. See: Williams, G. H. et al. in ref 27.
83. Mulliken, R. S.; Person, W. B. Molecular Complexes: A Lecture and Reprint Volume; Wiley: New York, 1969.
84. + ions has been demonstrated: Becker, H. G. O.; Israel, G.; Oertel, U.; Vetter, H.-U. J. Prakt. Chem. 1985, 327, 399 and related papers.
85. For a review of time-resolved (spectral) studies of photogenerated radical-ion pairs as in eq 16, see: Kochi, J. K. Acta Chem. Scand. 1990, 44, 409.
86. +), which yields the biaryl following deprotonation. For related examples, see: Parker, V. D.; Tilset, M. J. Am. Chem. Soc. 1987, 109, 2521. Bockman, T. M.; Kochi, J. K. J. Phys. Org. Chem. 1994, 7, 325.
87. +), which yields the biaryl following deprotonation. For related examples, see: Parker, V. D.; Tilset, M. J. Am. Chem. Soc. 1987, 109, 2521. Bockman, T. M.; Kochi, J. K. J. Phys. Org. Chem. 1994, 7, 325.
88. For some examples in which charge-transfer complexes (that contain very good electron donors) readily undergo thermal electron transfer as in eq 17, see: Kochi, J. K. Adv. Phys. Org. Chem. 1994, 29, 185 and related papers.
89. Estimated from: Elofson, R. M.; Gadallah, F. F. J. Org. Chem. 1969, 34, 854. Compare: Kochi, J. K. J. Am. Chem. Soc. 1955, 77, 3208.
90. Estimated from: Elofson, R. M.; Gadallah, F. F. J. Org. Chem. 1969, 34, 854. Compare: Kochi, J. K. J. Am. Chem. Soc. 1955, 77, 3208.
91. + is roughly isergonic, and the rate of electron transfer is thus expected to be very fast (see GEAR simulation in the Experimental Section).
92. See, e.g.: Nonhebel, D. C.; Walton, J. C. Free-Radical Chemistry; Cambridge: London, 1974; p 356.
93. (a) Iodide efficiencies approaching 100% in Figure 3 are to be contrasted with the more limited escape efficiencies measured in other azo decompositions. See: Koenig, T.; Fischer, H. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. I, p 157.
94. -] cannot be evaluated. Compare the CIDNP observations of Becker et al. in ref 46.
95. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry; Dekker: New York, 1993; p 207.