Alkylation of Pyridinium Acceptors via Thermal and Photoinduced Electron Transfer in Charge-Transfer Salts with Organoborates

Organometallics

Volumn 18, Issue 2, 1999, Pages 161-172

  Zhu, Dunming ^a   Kochi, Jay K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000601926     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9808054     Document Type: Article

References (89)

1. For some reviews, see: (a) Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; Wiley: New York, 1980. (b) Lipshutz, B. H.; Sengupta, S. In Organic Reaction; John Wiley & Sons: New York, 1992; Vol. 41, Chapter 2, pp 135-631. (c) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 386-403.
2. For some reviews, see: (a) Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; Wiley: New York, 1980. (b) Lipshutz, B. H.; Sengupta, S. In Organic Reaction; John Wiley & Sons: New York, 1992; Vol. 41, Chapter 2, pp 135-631. (c) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 386-403.
3. For some reviews, see: (a) Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; Wiley: New York, 1980. (b) Lipshutz, B. H.; Sengupta, S. In Organic Reaction; John Wiley & Sons: New York, 1992; Vol. 41, Chapter 2, pp 135-631. (c) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 386-403.
4. For some recent leading papers, see: (a) Uchiyama, M.; Furumoto, S.; Saito, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1997, 119, 11425. (b) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1996, 118, 8733. (c) Lipshutz, B. H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. SYNLETT 1997, 477. (d) Kjonaas, R. A.; Hoffer, R. K. J. Org. Chem. 1988, 53, 4133. (e) Nakamura, E.; Mon, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4881. (f) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900. (g) Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377.
5. For some recent leading papers, see: (a) Uchiyama, M.; Furumoto, S.; Saito, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1997, 119, 11425. (b) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1996, 118, 8733. (c) Lipshutz, B. H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. SYNLETT 1997, 477. (d) Kjonaas, R. A.; Hoffer, R. K. J. Org. Chem. 1988, 53, 4133. (e) Nakamura, E.; Mon, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4881. (f) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900. (g) Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377.
6. For some recent leading papers, see: (a) Uchiyama, M.; Furumoto, S.; Saito, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1997, 119, 11425. (b) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1996, 118, 8733. (c) Lipshutz, B. H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. SYNLETT 1997, 477. (d) Kjonaas, R. A.; Hoffer, R. K. J. Org. Chem. 1988, 53, 4133. (e) Nakamura, E.; Mon, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4881. (f) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900. (g) Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377.
7. For some recent leading papers, see: (a) Uchiyama, M.; Furumoto, S.; Saito, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1997, 119, 11425. (b) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1996, 118, 8733. (c) Lipshutz, B. H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. SYNLETT 1997, 477. (d) Kjonaas, R. A.; Hoffer, R. K. J. Org. Chem. 1988, 53, 4133. (e) Nakamura, E.; Mon, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4881. (f) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900. (g) Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377.
8. For some recent leading papers, see: (a) Uchiyama, M.; Furumoto, S.; Saito, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1997, 119, 11425. (b) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1996, 118, 8733. (c) Lipshutz, B. H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. SYNLETT 1997, 477. (d) Kjonaas, R. A.; Hoffer, R. K. J. Org. Chem. 1988, 53, 4133. (e) Nakamura, E.; Mon, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4881. (f) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900. (g) Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377.
9. For some recent leading papers, see: (a) Uchiyama, M.; Furumoto, S.; Saito, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1997, 119, 11425. (b) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1996, 118, 8733. (c) Lipshutz, B. H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. SYNLETT 1997, 477. (d) Kjonaas, R. A.; Hoffer, R. K. J. Org. Chem. 1988, 53, 4133. (e) Nakamura, E.; Mon, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4881. (f) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900. (g) Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377.
10. For some recent leading papers, see: (a) Uchiyama, M.; Furumoto, S.; Saito, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1997, 119, 11425. (b) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1996, 118, 8733. (c) Lipshutz, B. H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. SYNLETT 1997, 477. (d) Kjonaas, R. A.; Hoffer, R. K. J. Org. Chem. 1988, 53, 4133. (e) Nakamura, E.; Mon, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4881. (f) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900. (g) Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377.
11. (a) Negishi, E. J. Organomet. Chem. 1976, 108, 281.
12. (b) Negishi, E.; Chin, K. W.; Yoshida, T. J. Org. Chem. 1975, 40, 1676.
13. (c) Negishi, E.; Abramovitch, A.; Merrill, R. E. J. Chem. Soc., Chem. Commun. 1975, 138.
14. (a) Hunter, R.; Michael, J. P.; Tomlinson, G. D. Tetrahedron 1994, 50, 871.
15. (b) Miyaura, N.; Itoh, M.; Suzuki, A. Bull. Chem. Soc. Jpn. 1977, 50, 2199.
16. (c) Miyaura, N.; Itoh, M.; Suzuki, A. Synthesis 1976, 618.
17. Billing, R.; Rehorek, D.; Hennig, H. Topics Curr. Chem. 1990, 158, 151.
18. (a) Eaton, D. F. Pure Appl. Chem. 1984, 56, 1191.
19. (b) Gottschalk, P.; Schuster, G. B. U.S. Patent 4,772,541, 1988 (Chem. Abstr. 1987, 107, 187434n).
20. (c) Gottschalk, P.; Neckers, D. C.; Schuster, G. B. U.S. Patent 4,772,530, 1988 (Chem. Abstr. 1987, 107, 187434n).
21. (d) Farid, S. Y.; Moody, R. E. U.S. Patent 4,859,572, 1989 (Chem. Abstr. 1990, 112, 88310r).
22. (e) Satomura, M.; Iwakura, K.; Igarashi, A. U.S. Patent 4,847,236, 1989 (Chem. Abstr. 1988, 109, 160719p).
23. (f) Yamaguchi, J., Masaki, O.; Takanori, H. U.S. Patent 4,902,604, 1990 (Chem. Abstr. 1989, 111, 244332m).
24. (g) Koike, M.; Kita, N. U.S. Patent 4,950,581, 1990 (Chem. Abstr. 1989, 110, 183030s).
25. (h) Kawamura, K.; Okamoto, Y. U.S. Patent 4,971,891, 1990 (Chem. Abstr. 1989, 111, 222173h).
26. (i) Shanklin, M. S.; Gottschalk, P.; Adair, P. C. U.S. Patent 5,055,372, 1991 (Chem. Abstr. 1992, 116, 265621y).
27. (j) Marino, T.; DeRaaff, A. M.; Neckers, D. C. Rad Tech 96' North Am. UV/ED Conf. Proc. 1996, 7.
28. (k) Neckers, D. C.; Sarker, A. M.; Hassoon, S. A.; Polykarpov, A. Y.; DeRaaff, A. M.; Marino, T. L. PCT Int. Appl. WO 97 21,737, 1995 (Chem. Abstr. 1997, 127, 122109d).
29. (l) For an early review, see: Dietliker, J. Photochemical and Radiation Curing; Oldring, P. K. T., Ed.; SITA: London, 1990.
30. (a) Chatterjee, S.; Davis, P. D.; Gottschalk, P.; Kurz, M. E.; Sauerwein, B.; Yang, X.; Schuster, G. B. J. Am. Chem. Soc. 1990, 112, 6329.
31. (b) Schuster, G. B. Pure Appl. Chem. 1990, 62, 1565.
32. (c) Chrisope, D. R.; Schuster, G. B. Organometallics 1989, 8, 2737.
33. (d) Chatterjee, S.; Davis, P. D.; Schuster, G. B.; Gottschalk, P. J. Am. Chem. Soc. 1988 110, 2326.
34. (a) Hassoon, S.; Sarker, A.; Polykarpov, A. Y.; Rodgers, M. A. J.; Neckers, D. C. J. Phys. Chem. 1996, 100, 12386.
35. (b) Hassoon, S.; Sarker, A.; Rodgers, M. A. J.; Neeckers, D. C. J. Am. Chem. Soc. 1995, 117, 11369.
36. (c) Hassoon, S.; Neckers, D. C. J. Phys. Chem. 1995, 99, 9416.
37. (d) Feng, K.; Zang, H.; Martin, D.; Marino, T. L.; Neckers, D. C. J. Polym. Sci. (A) 1998, 36, 1667.
38. (e) Etter, M. C.; Holmes, B. N.; Kress, R. B.; Filipovich, G. Isr. J. Chem. 1985, 25, 264.
39. (a) Bockman, T. M.; Cho, H.-C.; Kochi, J. K. Organometallics 1995, 14, 5221.
40. (b) Bockman, T. M.; Kochi, J. K. New J. Chem. 1992, 16, 39.
41. (c) Bockman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 4669.
42. (d) Calderazzo, F.; Pampaloni, G.; Pelizzi, G.; Vitali, F. Organometallics 1988, 7, 1083.
43. The green solid was identified as a mixture of N,N′-dimethyl-9,9′-biacridanyl, bis(N-methylacridanyl)methane, 9,10-dimethylacridane, 9-methylacridane, and 9-methyl-10-acridanone.
44. - as supporting electrolyte.
45. Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 811.
46. (a) Taba, Y.; Yasuike, M.; Usui, Y. J. Chem. Soc., Chem. Commun. 1997, 675.
47. (b) Nagamura, T. Pure Appl. Chem. 1996, 68, 1449.
48. (c) Nagamura, T.; Sakai, K. J. Chem. Soc., Chem. Commun. 1986, 810.
49. The van der Waals radius of the methyl group is 2.0 Å, and the half-thickness of the aromatic molecule is taken as 1.70 Å. Pauling L. The Nature of the Chemical Bonds, 3nd ed.; Cornell Unversity Press: Ithaca, 1960.
50. (a) Barr, D.; Snaith, R.; Mulvey, R. E.; Perkins, P. G. Polyhedron 1988, 7, 2119.
51. (b) Rhine, W. E.; Stucky, G.; Peterson, S. W. J. Am. Chem. Soc. 1975, 97, 6401.
52. Each of the two isoquinolinium cations was in contact with two phenyl groups from two methyltriphenylborate anions, with one being near the positively charged nitrogen atom and the other being slightly overlapped with the aromatic acceptor ring at the other end (Figure 5). This donor-acceptor orientation is likely to result from the π-π interaction between the phenyl group and the isoquinolinium ring.
53. (a) Murphy, S.; Yang, X. Q.; Schuster, G. B. J. Org. Chem. 1995, 60, 2411.
54. (b) Koska, N. A.; Wilson, S. R.; Schuster, G. B. J. Am. Chem. Soc. 1993, 115, 11628.
55. (c) Yang, X. Q.; Zactsev, A.; Sauerwein, B.; Murphy, S.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 793.
56. (a) Bockman, T. M.; Kochi, J. K. In Photosensitization and Photocatalysis Using Inorganic and Organometallic Compounds; Kalyanasundaram, K., Gratzel, M., Eds.; Kluwer Academic Publishers: The Netherlands, 1993; p 407.
57. (b) Kochi, J. K.; Bockman, T. M. Adv. Organomet. Chem. 1991, 33, 52.
58. (a) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223.
59. (b) Bradley, W.; Jeffrey, S. J. Chem. Soc. 1954, 2770.
60. (c) Francis, R.; Davis, W.; Wisener, J. J. Org. Chem. 1974, 39, 59.
61. (d) Piers, E.; Sauey, M. Can. J. Chem. 1974, 52, 3563.
62. Irradiation was carried out with a cutoff filter (>370 or 410 nm), so that only the charge-transfer band of the pyridinium borates was irradiated.
63. 22d respectively.
64. (a) Lan, J. Y.; Schuster, G. B. Tetrahedron Lett. 1986, 27, 4261.
65. (b) Lan, J. Y.; Schuster, G. B. J. Am. Chem. Soc. 1985, 107, 6710.
66. (c) Matsuoka, M.; Hikida, T.; Murobushi, K.; Hosoda, Y. J. Chem. Soc., Chem. Commun. 1993, 299.
67. (d) Lund, T. Acta Chem. Scand. 1996, 50, 64.
68. Kosower, E. M. Prog. Phys. Org. Chem. 1965, 3, 81.
69. Kochi, J. K. Adv. Phys. Org. Chem. 1994, 29, 185.
70. (a) Schwarz, M.; Hermolin, J.; Kirowa-Eisner, E. J. Electroanal. Chem. 1987, 220, 139.
71. (b) Oturan, M. A.; Dostert, P.; Benedetti, M. S. J. Electroanal. Chem. 1988, 242, 171.
72. (c) Carelli, I.; Cardinali, M. E.; Casini, A.; Arnone, A. J. Org. Chem. 1976, 41, 3967.
73. Bancroft, E. E.; Blount, H. N. J. Am. Chem. Soc. 1979, 101, 3692.
74. -1; see ref 7.
75. March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992; p 186.
76. The LUMO of pyridinium cations is a π* orbital centered on the aromatic ring. (a) Grossi, L.; Minisci, F.; Pedulli, G. F. J. Chem. Soc., Perkin Trans. 2 1977, 943. (b) Itoh, M.; Nagakura, S. J. Am. Chem. Soc. 1967, 89, 3959.
77. The LUMO of pyridinium cations is a π* orbital centered on the aromatic ring. (a) Grossi, L.; Minisci, F.; Pedulli, G. F. J. Chem. Soc., Perkin Trans. 2 1977, 943. (b) Itoh, M.; Nagakura, S. J. Am. Chem. Soc. 1967, 89, 3959.
78. Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647.
79. (a) Hurd, D. T. J. Org. Chem. 1948, 13, 711.
80. (b) Damico, R. J. Org. Chem. 1964, 29, 1971.
81. Negishi, E.; Idacavage, M. J.; Chiu, K.-W.; Yoshida, T.; Abramovitch, A.; Goettel, M. E.; Silveria, A., Jr.; Bretherick, H. D. J. Chem. Soc., Perkin Trans. 2 1978, 1225.
82. Bockman, T. M.; Kochi, J. K. J. Phys. Org. Chem. 1997, 10, 542.
83. (a) Kitane, S.; Tshiamala, K.; Laude, B.; Vebrel, J.; Ceratti, E. Tetrahedron 1985, 42, 3737.
84. (b) See ref 19b.
85. Heitsch, C. H. Inorg. Chem. 1964, 4, 1019.
86. -] have been deposited with the Cambridge Crystallographic Data Centre. They can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1eZ, U.K.
87. Sheldrick, G. M. SHELXS86, Program for the Solution of Crystal Structures; University of Göttingen, Germany, 1985.
88. Sheldrick, G. M. SHELXL93, Program for the Refinement of Crystal Structures; University of Göttingen, Germany, 1993.
89. 1 resulted in the same kind of disorder. Since the disorder did not result from the proper symmetry choice, the crystal can be a centrosymmetric twin of two chiral components (which we also considered). The refinement in the centrosymmetric space group Cmcm provided the best precision relative to noncentrosymmetric and twinned models.