Direct oxidative carbon-carbon bond formation using the 'cation pool' Method. 1. Generation of iminium cation pools and their reaction with carbon nucleophiles

Journal of the American Chemical Society

Volumn 121, Issue 41, 1999, Pages 9546-9549

  Yoshida, Jun Ichi ^a   Suga, Seiji ^a   Suzuki, Shinkiti ^a   Kinomura, Naoya ^a   Yamamoto, Atsushi ^a   Fujiwara, Kazuyuki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID; CARBON; CATION;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; ELECTROLYSIS; LOW TEMPERATURE; OXIDATION; REACTION ANALYSIS;

EID: 0032705881     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9920112     Document Type: Article

References (39)

1. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S., Eds.; Pergamon Press: Oxford, 1991; Vol. 7 (Oxidation).
2. For example: (a) Olah, G. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1393-1405. (b) Stable Carbocation Chemistry; Prakash, G. K. S., Schleyer, P. v. R., Eds.; Wiley-Interscience: New York, 1997.
3. For example: (a) Olah, G. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1393-1405. (b) Stable Carbocation Chemistry; Prakash, G. K. S., Schleyer, P. v. R., Eds.; Wiley-Interscience: New York, 1997.
4. For an electrochemical example, see: (a) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (b) Shono, T. Tetrahedron 1984, 40, 811-850. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand., Ser. B 1979, 33, 69-72. (d) Mon, M.; Kagechika, K.; Sasai, H.; Shibasaki, M. Tetrahedron 1991, 47, 531-540. (e) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106-10112. (f) Danielmeier, K.; Schierle, K.; Steckhan, E. Tetrahedron 1996, 52, 9743-9754. For an example using Ru catalyzed oxidation, see: Naota, T.; Nakato, T.; Murahasi, S. Tetrahedron Lett. 1990, 31, 7475-7478.
5. For an electrochemical example, see: (a) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (b) Shono, T. Tetrahedron 1984, 40, 811-850. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand., Ser. B 1979, 33, 69-72. (d) Mon, M.; Kagechika, K.; Sasai, H.; Shibasaki, M. Tetrahedron 1991, 47, 531-540. (e) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106-10112. (f) Danielmeier, K.; Schierle, K.; Steckhan, E. Tetrahedron 1996, 52, 9743-9754. For an example using Ru catalyzed oxidation, see: Naota, T.; Nakato, T.; Murahasi, S. Tetrahedron Lett. 1990, 31, 7475-7478.
6. For an electrochemical example, see: (a) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (b) Shono, T. Tetrahedron 1984, 40, 811-850. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand., Ser. B 1979, 33, 69-72. (d) Mon, M.; Kagechika, K.; Sasai, H.; Shibasaki, M. Tetrahedron 1991, 47, 531-540. (e) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106-10112. (f) Danielmeier, K.; Schierle, K.; Steckhan, E. Tetrahedron 1996, 52, 9743-9754. For an example using Ru catalyzed oxidation, see: Naota, T.; Nakato, T.; Murahasi, S. Tetrahedron Lett. 1990, 31, 7475-7478.
7. For an electrochemical example, see: (a) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (b) Shono, T. Tetrahedron 1984, 40, 811-850. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand., Ser. B 1979, 33, 69-72. (d) Mon, M.; Kagechika, K.; Sasai, H.; Shibasaki, M. Tetrahedron 1991, 47, 531-540. (e) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106-10112. (f) Danielmeier, K.; Schierle, K.; Steckhan, E. Tetrahedron 1996, 52, 9743-9754. For an example using Ru catalyzed oxidation, see: Naota, T.; Nakato, T.; Murahasi, S. Tetrahedron Lett. 1990, 31, 7475-7478.
8. For an electrochemical example, see: (a) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (b) Shono, T. Tetrahedron 1984, 40, 811-850. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand., Ser. B 1979, 33, 69-72. (d) Mon, M.; Kagechika, K.; Sasai, H.; Shibasaki, M. Tetrahedron 1991, 47, 531-540. (e) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106-10112. (f) Danielmeier, K.; Schierle, K.; Steckhan, E. Tetrahedron 1996, 52, 9743-9754. For an example using Ru catalyzed oxidation, see: Naota, T.; Nakato, T.; Murahasi, S. Tetrahedron Lett. 1990, 31, 7475-7478.
9. For an electrochemical example, see: (a) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (b) Shono, T. Tetrahedron 1984, 40, 811-850. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand., Ser. B 1979, 33, 69-72. (d) Mon, M.; Kagechika, K.; Sasai, H.; Shibasaki, M. Tetrahedron 1991, 47, 531-540. (e) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106-10112. (f) Danielmeier, K.; Schierle, K.; Steckhan, E. Tetrahedron 1996, 52, 9743-9754. For an example using Ru catalyzed oxidation, see: Naota, T.; Nakato, T.; Murahasi, S. Tetrahedron Lett. 1990, 31, 7475-7478.
10. For an electrochemical example, see: (a) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (b) Shono, T. Tetrahedron 1984, 40, 811-850. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand., Ser. B 1979, 33, 69-72. (d) Mon, M.; Kagechika, K.; Sasai, H.; Shibasaki, M. Tetrahedron 1991, 47, 531-540. (e) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106-10112. (f) Danielmeier, K.; Schierle, K.; Steckhan, E. Tetrahedron 1996, 52, 9743-9754. For an example using Ru catalyzed oxidation, see: Naota, T.; Nakato, T.; Murahasi, S. Tetrahedron Lett. 1990, 31, 7475-7478.
11. - is relatively high. It is also noteworthy that the CN group is strongly electron-withdrawing so that the oxidation potential of the product is expected to be much higher than the starting material. Electrochemical cyanation: (a) Chiba, T.; Tanaka, Y. J. Org. Chem., 1977, 42, 2973-2977. Chemical oxidative cyanation: (b) Chen, C.-K.; Hortmann, A. G.; Marzabadi, M. R. J. Am. Chem. Soc. 1988, 110, 4829-4831. Some amines having very low oxidation potentials, such as dimethylmesidine, could exceptionally be substrates for the electrooxidative C-C bond formation: (c) Renaud, R. N.; Bérubé, D.; Stephens, C. J. Can. J. Chem. 1983, 61, 1379-1382.
12. - is relatively high. It is also noteworthy that the CN group is strongly electron-withdrawing so that the oxidation potential of the product is expected to be much higher than the starting material. Electrochemical cyanation: (a) Chiba, T.; Tanaka, Y. J. Org. Chem., 1977, 42, 2973-2977. Chemical oxidative cyanation: (b) Chen, C.-K.; Hortmann, A. G.; Marzabadi, M. R. J. Am. Chem. Soc. 1988, 110, 4829-4831. Some amines having very low oxidation potentials, such as dimethylmesidine, could exceptionally be substrates for the electrooxidative C-C bond formation: (c) Renaud, R. N.; Bérubé, D.; Stephens, C. J. Can. J. Chem. 1983, 61, 1379-1382.
13. - is relatively high. It is also noteworthy that the CN group is strongly electron-withdrawing so that the oxidation potential of the product is expected to be much higher than the starting material. Electrochemical cyanation: (a) Chiba, T.; Tanaka, Y. J. Org. Chem., 1977, 42, 2973-2977. Chemical oxidative cyanation: (b) Chen, C.-K.; Hortmann, A. G.; Marzabadi, M. R. J. Am. Chem. Soc. 1988, 110, 4829-4831. Some amines having very low oxidation potentials, such as dimethylmesidine, could exceptionally be substrates for the electrooxidative C-C bond formation: (c) Renaud, R. N.; Bérubé, D.; Stephens, C. J. Can. J. Chem. 1983, 61, 1379-1382.
14. Electrochemical α-oxidation of amine derivatives: (a) Shono, T. Electroorganic Chemistry as a New Tool in Organic Synthesis; Springer-Verlag: Berlin, 1984. Transition metal promoted α-oxidation of amine derivatives: (b) Murahashi, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 2443-2465.
15. Electrochemical α-oxidation of amine derivatives: (a) Shono, T. Electroorganic Chemistry as a New Tool in Organic Synthesis; Springer- Verlag: Berlin, 1984. Transition metal promoted α-oxidation of amine derivatives: (b) Murahashi, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 2443-2465.
16. Reviews for the synthetic utility of acyliminium cation, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416. (b) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047- 1082. (c) Zaugg, H. E. Synthesis 1984, 85-110. (d) Zaugg, H. E. Synthesis 1984, 181-212.
17. Reviews for the synthetic utility of acyliminium cation, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416. (b) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047-1082. (c) Zaugg, H. E. Synthesis 1984, 85-110. (d) Zaugg, H. E. Synthesis 1984, 181-212.
18. Reviews for the synthetic utility of acyliminium cation, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416. (b) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047- 1082. (c) Zaugg, H. E. Synthesis 1984, 85-110. (d) Zaugg, H. E. Synthesis 1984, 181-212.
19. Reviews for the synthetic utility of acyliminium cation, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416. (b) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047- 1082. (c) Zaugg, H. E. Synthesis 1984, 85-110. (d) Zaugg, H. E. Synthesis 1984, 181-212.
20. For example: (a) Sakurai, H. Pure Appl. Chem. 1982, 54, 1-22. (b) Chan, T. H.; Fleming, I. Synthesis 1979, 761-786.
21. For example: (a) Sakurai, H. Pure Appl. Chem. 1982, 54, 1-22. (b) Chan, T. H.; Fleming, I. Synthesis 1979, 761-786.
22. The conventional electrochemical oxidation of carbamates using methanol as a nucleophile has been developed: (a) Shono, T.; Hamaguchi, H.; Matsumura, Y. J. Am. Chem. Soc. 1975, 97, 4264-4268. (b) Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth. 1985, 63, 206-213. The oxidative α-methoxylation of amides has also been reported: (c) Ross, S. D.; Finkelstein, M.; Peterson, R. C. J. Am. Chem. Soc. 1966, 80, 4657- 4660. (d) Nyberg, K.; Servin, R. Acta Chem. Scand., Ser. B 1976, 30, 640- 642.
23. The conventional electrochemical oxidation of carbamates using methanol as a nucleophile has been developed: (a) Shono, T.; Hamaguchi, H.; Matsumura, Y. J. Am. Chem. Soc. 1975, 97, 4264-4268. (b) Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth. 1985, 63, 206-213. The oxidative α-methoxylation of amides has also been reported: (c) Ross, S. D.; Finkelstein, M.; Peterson, R. C. J. Am. Chem. Soc. 1966, 80, 4657- 4660. (d) Nyberg, K.; Servin, R. Acta Chem. Scand., Ser. B 1976, 30, 640- 642.
24. The conventional electrochemical oxidation of carbamates using methanol as a nucleophile has been developed: (a) Shono, T.; Hamaguchi, H.; Matsumura, Y. J. Am. Chem. Soc. 1975, 97, 4264-4268. (b) Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth. 1985, 63, 206-213. The oxidative α-methoxylation of amides has also been reported: (c) Ross, S. D.; Finkelstein, M.; Peterson, R. C. J. Am. Chem. Soc. 1966, 80, 4657-4660. (d) Nyberg, K.; Servin, R. Acta Chem. Scand., Ser. B 1976, 30, 640- 642.
25. The conventional electrochemical oxidation of carbamates using methanol as a nucleophile has been developed: (a) Shono, T.; Hamaguchi, H.; Matsumura, Y. J. Am. Chem. Soc. 1975, 97, 4264-4268. (b) Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth. 1985, 63, 206-213. The oxidative α-methoxylation of amides has also been reported: (c) Ross, S. D.; Finkelstein, M.; Peterson, R. C. J. Am. Chem. Soc. 1966, 80, 4657- 4660. (d) Nyberg, K.; Servin, R. Acta Chem. Scand., Ser. B 1976, 30, 640-642.
26. For the effect of the counteranion on reactivity, see: Yamaguchi, R.; Hatano, B.; Nakayasu, T.; Kozima, S. Tetrahedron Lett. 1997, 38, 403-406.
27. 1H NMR spectroscopy: (d) Bose, A. K.; Spiegelman, G.; Manhas, M. S. Tetrahedron Lett. 1971, 3167-3170.
28. 1H NMR spectroscopy: (d) Bose, A. K.; Spiegelman, G.; Manhas, M. S. Tetrahedron Lett. 1971, 3167-3170.
29. 1H NMR spectroscopy: (d) Bose, A. K.; Spiegelman, G.; Manhas, M. S. Tetrahedron Lett. 1971, 3167-3170.
30. 1H NMR spectroscopy: (d) Bose, A. K.; Spiegelman, G.; Manhas, M. S. Tetrahedron Lett. 1971, 3167-3170.
31. For example: (a) Borman, S. Chem. Eng. News 1996 (February 12), 28-73. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Borman, S. Chem. Eng. News 1997 (February 24), 43-62. (d) Borman, S. Chem. Eng. News 1999 (March 3), 33-48. (e) Dagani, R. Chem. Eng. News 1999 (March 3) 51-60 and references therein.
32. For example: (a) Borman, S. Chem. Eng. News 1996 (February 12), 28-73. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Borman, S. Chem. Eng. News 1997 (February 24), 43-62. (d) Borman, S. Chem. Eng. News 1999 (March 3), 33-48. (e) Dagani, R. Chem. Eng. News 1999 (March 3) 51-60 and references therein.
33. For example: (a) Borman, S. Chem. Eng. News 1996 (February 12), 28-73. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Borman, S. Chem. Eng. News 1997 (February 24), 43-62. (d) Borman, S. Chem. Eng. News 1999 (March 3), 33-48. (e) Dagani, R. Chem. Eng. News 1999 (March 3) 51-60 and references therein.
34. For example: (a) Borman, S. Chem. Eng. News 1996 (February 12), 28-73. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Borman, S. Chem. Eng. News 1997 (February 24), 43-62. (d) Borman, S. Chem. Eng. News 1999 (March 3), 33-48. (e) Dagani, R. Chem. Eng. News 1999 (March 3) 51-60 and references therein.
35. For example: (a) Borman, S. Chem. Eng. News 1996 (February 12), 28-73. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Borman, S. Chem. Eng. News 1997 (February 24), 43-62. (d) Borman, S. Chem. Eng. News 1999 (March 3), 33-48. (e) Dagani, R. Chem. Eng. News 1999 (March 3) 51-60 and references therein.
36. For example: (a) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (b) Graven, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489- 509. (c) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826. (d) Cheng, S.; Commer, D. D.; Williams, J. P. Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567-2573 and references therein.
37. For example: (a) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (b) Graven, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (c) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826. (d) Cheng, S.; Commer, D. D.; Williams, J. P. Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567-2573 and references therein.
38. For example: (a) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (b) Graven, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489- 509. (c) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826. (d) Cheng, S.; Commer, D. D.; Williams, J. P. Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567-2573 and references therein.
39. For example: (a) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (b) Graven, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489- 509. (c) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826. (d) Cheng, S.; Commer, D. D.; Williams, J. P. Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567-2573 and references therein.