C-C bond formation between isocyanide and β,β-difluoroalkene moieties via electron transfer: Fluorinated quinoline and biquinoline syntheses

Synlett

Volumn , Issue 7, 2004, Pages 1219-1222

  Ichikawa, Junji ^a   Mori, Takashi ^a   Miyazaki, Hiroyuki ^b   Wada, Yukinori ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Cyclizations; Electron transfer; Fluorinated alkenes; Fluorinated quinolines; Isocyanides

Indexed keywords

ALKENE DERIVATIVE; ANION; CARBON; CYANIDE; FLUORINE; LITHIUM DERIVATIVE; QUINOLINE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL REACTION; DRUG SYNTHESIS; ELECTRON TRANSPORT; FLUORINATION; SUBSTITUTION REACTION;

EID: 2942741318     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-825599     Document Type: Article

References (41)

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11. For the synthesis of fluoroquinolines, see: (a) Wada, Y.; Mori, T.; Ichikawa, J. Chem. Lett. 2003, 1000. (b) Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455. (c) Chambers, R. D.; Parsons, M.; Sandford, G.; Skinner, C. J.; Atherton, M. J.; Moilliet, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 803; and references therein. (d) Strekowski, L.; Kiselyov, A. S.; Hojjat, M. J. Org. Chem. 1994, 59, 5886. (e) Shi, G.-Q.; Takagishi, S.; Schlosser, M. Tetrahedron 1994, 50, 1129.
12. For the synthesis of fluoroquinolines, see: (a) Wada, Y.; Mori, T.; Ichikawa, J. Chem. Lett. 2003, 1000. (b) Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455. (c) Chambers, R. D.; Parsons, M.; Sandford, G.; Skinner, C. J.; Atherton, M. J.; Moilliet, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 803; and references therein. (d) Strekowski, L.; Kiselyov, A. S.; Hojjat, M. J. Org. Chem. 1994, 59, 5886. (e) Shi, G.-Q.; Takagishi, S.; Schlosser, M. Tetrahedron 1994, 50, 1129.
13. For the synthesis of fluoroquinolines, see: (a) Wada, Y.; Mori, T.; Ichikawa, J. Chem. Lett. 2003, 1000. (b) Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455. (c) Chambers, R. D.; Parsons, M.; Sandford, G.; Skinner, C. J.; Atherton, M. J.; Moilliet, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 803; and references therein. (d) Strekowski, L.; Kiselyov, A. S.; Hojjat, M. J. Org. Chem. 1994, 59, 5886. (e) Shi, G.-Q.; Takagishi, S.; Schlosser, M. Tetrahedron 1994, 50, 1129.
14. For the synthesis of 2,4-disubstituted quinolines, see: (a) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (b) Kobayashi, K.; Yoneda, K.; Mano, M.; Morikawa, O.; Konishi, H. Chem. Lett. 2003, 76. (c) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485. See also for recent reports on the construction of quinoline framework: (d) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209. (e) Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885; and references therein. For the synthesis of quinolines from aryl isocyanides, see the following and references cited therein: (f) Kobayashi, K.; Yoneda, K.; Mizumoto, T.; Umakoshi, H.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 2003, 44, 473. (g) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215. (h) Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
15. For the synthesis of 2,4-disubstituted quinolines, see: (a) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (b) Kobayashi, K.; Yoneda, K.; Mano, M.; Morikawa, O.; Konishi, H. Chem. Lett. 2003, 76. (c) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485. See also for recent reports on the construction of quinoline framework: (d) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209. (e) Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885; and references therein. For the synthesis of quinolines from aryl isocyanides, see the following and references cited therein: (f) Kobayashi, K.; Yoneda, K.; Mizumoto, T.; Umakoshi, H.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 2003, 44, 473. (g) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215. (h) Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
16. For the synthesis of 2,4-disubstituted quinolines, see: (a) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (b) Kobayashi, K.; Yoneda, K.; Mano, M.; Morikawa, O.; Konishi, H. Chem. Lett. 2003, 76. (c) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485. See also for recent reports on the construction of quinoline framework: (d) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209. (e) Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885; and references therein. For the synthesis of quinolines from aryl isocyanides, see the following and references cited therein: (f) Kobayashi, K.; Yoneda, K.; Mizumoto, T.; Umakoshi, H.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 2003, 44, 473. (g) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215. (h) Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
17. For the synthesis of 2,4-disubstituted quinolines, see: (a) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (b) Kobayashi, K.; Yoneda, K.; Mano, M.; Morikawa, O.; Konishi, H. Chem. Lett. 2003, 76. (c) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485. See also for recent reports on the construction of quinoline framework: (d) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209. (e) Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885; and references therein. For the synthesis of quinolines from aryl isocyanides, see the following and references cited therein: (f) Kobayashi, K.; Yoneda, K.; Mizumoto, T.; Umakoshi, H.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 2003, 44, 473. (g) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215. (h) Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
18. For the synthesis of 2,4-disubstituted quinolines, see: (a) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (b) Kobayashi, K.; Yoneda, K.; Mano, M.; Morikawa, O.; Konishi, H. Chem. Lett. 2003, 76. (c) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485. See also for recent reports on the construction of quinoline framework: (d) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209. (e) Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885; and references therein. For the synthesis of quinolines from aryl isocyanides, see the following and references cited therein: (f) Kobayashi, K.; Yoneda, K.; Mizumoto, T.; Umakoshi, H.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 2003, 44, 473. (g) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215. (h) Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
19. For the synthesis of 2,4-disubstituted quinolines, see: (a) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (b) Kobayashi, K.; Yoneda, K.; Mano, M.; Morikawa, O.; Konishi, H. Chem. Lett. 2003, 76. (c) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485. See also for recent reports on the construction of quinoline framework: (d) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209. (e) Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885; and references therein. For the synthesis of quinolines from aryl isocyanides, see the following and references cited therein: (f) Kobayashi, K.; Yoneda, K.; Mizumoto, T.; Umakoshi, H.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 2003, 44, 473. (g) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215. (h) Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
20. For the synthesis of 2,4-disubstituted quinolines, see: (a) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (b) Kobayashi, K.; Yoneda, K.; Mano, M.; Morikawa, O.; Konishi, H. Chem. Lett. 2003, 76. (c) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485. See also for recent reports on the construction of quinoline framework: (d) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209. (e) Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885; and references therein. For the synthesis of quinolines from aryl isocyanides, see the following and references cited therein: (f) Kobayashi, K.; Yoneda, K.; Mizumoto, T.; Umakoshi, H.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 2003, 44, 473. (g) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215. (h) Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
21. For the synthesis of 2,4-disubstituted quinolines, see: (a) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (b) Kobayashi, K.; Yoneda, K.; Mano, M.; Morikawa, O.; Konishi, H. Chem. Lett. 2003, 76. (c) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485. See also for recent reports on the construction of quinoline framework: (d) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209. (e) Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885; and references therein. For the synthesis of quinolines from aryl isocyanides, see the following and references cited therein: (f) Kobayashi, K.; Yoneda, K.; Mizumoto, T.; Umakoshi, H.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 2003, 44, 473. (g) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215. (h) Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
22. (a) Smart, B. E. In Organofluorine Chemistry, Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum: New York, 1994, Chap. 3.
23. (b) Lee, V. J. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Chap. 1.2.
24. (a) Gros, P.; Fort, Y. Eur. J. Org. Chem. 2002, 3375; and references therein.
25. (b) Gros, P.; Fort, Y.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1997, 3597.
26. McCombie, S. W. In Comprehensive Organic Synthesis, Vol. 8; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Chap. 4.2.
27. 3SnH or EtSH, this type of C-C bond formation is well known in the Fukuyama indole synthesis. See: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (b) Tokuyama, H.; Fukuyama, T. Chem. Rec. 2002, 2, 37.
28. 3SnH or EtSH, this type of C-C bond formation is well known in the Fukuyama indole synthesis. See: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (b) Tokuyama, H.; Fukuyama, T. Chem. Rec. 2002, 2, 37.
29. -1].
30. The cyclization similarly proceeded even in the dark. For electron transfer from triorganostannyl anions, see: Yammal, C. C.; Podesta, J. C.; Rossi, R. A. J. Org. Chem. 1992, 57, 5720.
31. For recent reports on biquinoline synthesis, see: (a) Uchida, Y.; Echikawa, N.; Oae, S. Heteroat. Chem. 1994, 5, 409. (b) Fort, Y.; Becker, S.; Caubère, P. Tetrahedron 1994, 50, 11893.
32. For recent reports on biquinoline synthesis, see: (a) Uchida, Y.; Echikawa, N.; Oae, S. Heteroat. Chem. 1994, 5, 409. (b) Fort, Y.; Becker, S.; Caubère, P. Tetrahedron 1994, 50, 11893.
33. Biquinolines are widely used as bulky, chelating nitrogen ligands. See for example: (a) Bhattacharyya, R.; Drago, R. S.; Abboud, K. A. Inorg. Chem. 1997, 36, 2913. (b) Gogoll, A.; Gomes, J.; Bergkvist, M.; Grennberg, H. Organometallics 1995, 14, 1354. (c) Kubow, S. A.; Marmion, M. E.; Takeuchi, K. J. Inorg. Chem. 1988, 27, 2761. See also for a chiral 2,2′-biquinoline N,N′-dioxide as an asymmetric catalyst: (d) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419.
34. Biquinolines are widely used as bulky, chelating nitrogen ligands. See for example: (a) Bhattacharyya, R.; Drago, R. S.; Abboud, K. A. Inorg. Chem. 1997, 36, 2913. (b) Gogoll, A.; Gomes, J.; Bergkvist, M.; Grennberg, H. Organometallics 1995, 14, 1354. (c) Kubow, S. A.; Marmion, M. E.; Takeuchi, K. J. Inorg. Chem. 1988, 27, 2761. See also for a chiral 2,2′-biquinoline N,N′-dioxide as an asymmetric catalyst: (d) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419.
35. Biquinolines are widely used as bulky, chelating nitrogen ligands. See for example: (a) Bhattacharyya, R.; Drago, R. S.; Abboud, K. A. Inorg. Chem. 1997, 36, 2913. (b) Gogoll, A.; Gomes, J.; Bergkvist, M.; Grennberg, H. Organometallics 1995, 14, 1354. (c) Kubow, S. A.; Marmion, M. E.; Takeuchi, K. J. Inorg. Chem. 1988, 27, 2761. See also for a chiral 2,2′-biquinoline N,N′-dioxide as an asymmetric catalyst: (d) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419.
36. Biquinolines are widely used as bulky, chelating nitrogen ligands. See for example: (a) Bhattacharyya, R.; Drago, R. S.; Abboud, K. A. Inorg. Chem. 1997, 36, 2913. (b) Gogoll, A.; Gomes, J.; Bergkvist, M.; Grennberg, H. Organometallics 1995, 14, 1354. (c) Kubow, S. A.; Marmion, M. E.; Takeuchi, K. J. Inorg. Chem. 1988, 27, 2761. See also for a chiral 2,2′-biquinoline N,N′-dioxide as an asymmetric catalyst: (d) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419.
37. +); found: 203.1128.
38. +); found: 404.2057.
39. 19F NMR. Over the course of the reaction, the corresponding ditin and tin hydride were produced probably via the tin radical.
40. 3SnLi, was reacted with 0.8 equiv of 1b (R = Et), unsymmetrical 4-butyl-4′-ethyl-3,3′-difluoro-2,2′-biquinoline was obtained in 59% yield (based on the consumed 1b).
41. Shimano, M.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 7727.