Pd(0)-Catalyzed Bismetallative Cyclization of Enynes in the Presence of Bu3SnSiMe3 Using N-Heterocyclic Carbene as a Ligand

Advanced Synthesis and Catalysis

Volumn 345, Issue 4, 2003, Pages 488-491

  Sato, Yoshihiro ^a   Imakuni, Noriko ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Bismetallation; Cyclization; Imidazol 2 ylidene ligands; N heterocyclic carbene ligands; Palladium; Silylstannane

Indexed keywords

CARBENOID; IMIDAZOLE DERIVATIVE; NITROGEN; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; METAL BINDING; ORGANIC CHEMISTRY;

EID: 0242438877     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200390055     Document Type: Article

References (45)

1. For reviews, see: I. Beletskaya, C. Moberg, Chem. Rev. 1999, 99, 3435.
2. For bismetallative cyclization, see: a) Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, T. Kawamura, J. Chem. Soc. Perkin Trans. 1 1995, 599; b) S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229; c) S.-y. Onozawa, Y. Hatanaka, N. Choi, M. Tanaka, Organometallics 1997, 16, 5389; d) M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; e) M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221; f) S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579; g) S.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; h) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416; i) M. Lautens, J. Mancuso, Synlett 2002, 394.
3. For bismetallative cyclization, see: a) Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, T. Kawamura, J. Chem. Soc. Perkin Trans. 1 1995, 599; b) S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229; c) S.-y. Onozawa, Y. Hatanaka, N. Choi, M. Tanaka, Organometallics 1997, 16, 5389; d) M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; e) M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221; f) S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579; g) S.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; h) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416; i) M. Lautens, J. Mancuso, Synlett 2002, 394.
4. For bismetallative cyclization, see: a) Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, T. Kawamura, J. Chem. Soc. Perkin Trans. 1 1995, 599; b) S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229; c) S.-y. Onozawa, Y. Hatanaka, N. Choi, M. Tanaka, Organometallics 1997, 16, 5389; d) M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; e) M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221; f) S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579; g) S.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; h) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416; i) M. Lautens, J. Mancuso, Synlett 2002, 394.
5. For bismetallative cyclization, see: a) Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, T. Kawamura, J. Chem. Soc. Perkin Trans. 1 1995, 599; b) S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229; c) S.-y. Onozawa, Y. Hatanaka, N. Choi, M. Tanaka, Organometallics 1997, 16, 5389; d) M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; e) M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221; f) S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579; g) S.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; h) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416; i) M. Lautens, J. Mancuso, Synlett 2002, 394.
6. For bismetallative cyclization, see: a) Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, T. Kawamura, J. Chem. Soc. Perkin Trans. 1 1995, 599; b) S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229; c) S.-y. Onozawa, Y. Hatanaka, N. Choi, M. Tanaka, Organometallics 1997, 16, 5389; d) M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; e) M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221; f) S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579; g) S.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; h) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416; i) M. Lautens, J. Mancuso, Synlett 2002, 394.
7. For bismetallative cyclization, see: a) Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, T. Kawamura, J. Chem. Soc. Perkin Trans. 1 1995, 599; b) S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229; c) S.-y. Onozawa, Y. Hatanaka, N. Choi, M. Tanaka, Organometallics 1997, 16, 5389; d) M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; e) M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221; f) S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579; g) S.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; h) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416; i) M. Lautens, J. Mancuso, Synlett 2002, 394.
8. For bismetallative cyclization, see: a) Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, T. Kawamura, J. Chem. Soc. Perkin Trans. 1 1995, 599; b) S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229; c) S.-y. Onozawa, Y. Hatanaka, N. Choi, M. Tanaka, Organometallics 1997, 16, 5389; d) M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; e) M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221; f) S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579; g) S.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; h) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416; i) M. Lautens, J. Mancuso, Synlett 2002, 394.
9. For bismetallative cyclization, see: a) Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, T. Kawamura, J. Chem. Soc. Perkin Trans. 1 1995, 599; b) S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229; c) S.-y. Onozawa, Y. Hatanaka, N. Choi, M. Tanaka, Organometallics 1997, 16, 5389; d) M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; e) M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221; f) S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579; g) S.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; h) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416; i) M. Lautens, J. Mancuso, Synlett 2002, 394.
10. For bismetallative cyclization, see: a) Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, T. Kawamura, J. Chem. Soc. Perkin Trans. 1 1995, 599; b) S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229; c) S.-y. Onozawa, Y. Hatanaka, N. Choi, M. Tanaka, Organometallics 1997, 16, 5389; d) M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; e) M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221; f) S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579; g) S.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; h) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416; i) M. Lautens, J. Mancuso, Synlett 2002, 394.
11. M. Mori, T. Hirose, H. Wakamatsu, N. Imakuni, Y. Sato, Organometallics 2001, 20, 1907.
12. A. J. Arduengo, III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361.
13. For reviews, see: a) W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1290; b) W. A. Herrmann, T. Weskamp, V. P. W. Böhm, Adv. Organomet. Chem. 2002, 48, 1; c) L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181; d) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39; e) W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 1997, 36, 2162.
14. For reviews, see: a) W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1290; b) W. A. Herrmann, T. Weskamp, V. P. W. Böhm, Adv. Organomet. Chem. 2002, 48, 1; c) L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181; d) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39; e) W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 1997, 36, 2162.
15. For reviews, see: a) W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1290; b) W. A. Herrmann, T. Weskamp, V. P. W. Böhm, Adv. Organomet. Chem. 2002, 48, 1; c) L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181; d) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39; e) W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 1997, 36, 2162.
16. For reviews, see: a) W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1290; b) W. A. Herrmann, T. Weskamp, V. P. W. Böhm, Adv. Organomet. Chem. 2002, 48, 1; c) L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181; d) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39; e) W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 1997, 36, 2162.
17. For reviews, see: a) W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1290; b) W. A. Herrmann, T. Weskamp, V. P. W. Böhm, Adv. Organomet. Chem. 2002, 48, 1; c) L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181; d) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39; e) W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 1997, 36, 2162.
18. a) W. A. Herrmann, C. P. Reisinger, M. Spiegler, J. Organomet. Chem. 1998, 557, 93;
19. b) V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, J. Organomet. Chem. 2000, 595, 186;
20. c) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804;
21. d) H. M. Lee, S. P. Nolan, Org. Lett. 2000, 2, 2053;
22. e) C. Zhang, M. L. Trudell, Tetrahedron Lett. 2000, 41, 595;
23. f) A. Fürstner, A. Leitner, Synlett 2001, 290.
24. a) J. Huang, S. P. Nolan, J. Am. Chem. Soc. 1999, 121, 9889;
25. for Ni-catalyzed Kumada-Tamao cross-coupling reactions using nucleophilic N-heterocyclic carbenes, see: b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. Int. Ed. 2000, 39, 1602.
26. a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. Int. Ed. Engl. 1995, 34, 2371;
27. b) W. A. Herrmann, J. Fischer, M. Elison, C. Köcher, G. R. J. Artus, Chem. Eur. J. 1996, 2, 772;
28. c) D. Enders, H. Gielen, G. Raabe, J. Runsink, H. Teles, Chem. Ber. 1996, 129, 1483;
29. d) D. S. McGuinness, M. J. Green, K. J. Cavell, B. W. Skelton, A. H. White, J. Organomet. Chem. 1998, 565, 165;
30. e) D. S. McGuinness, K. J. Cavell, Organometallics 1999, 18, 1596;
31. f) D. S. Clyne, J. Jin, E. Genest, J. C. Gallucci, T. V. RajanBabu, Org. Lett. 2000, 2, 1125;
32. g) C. Yang, H. M. Lee, S. P. Nolan, Org. Lett. 2001, 3, 1511.
33. a) J. Huang, G. Grasa, S. P. Nolan, Org. Lett. 1999, 1, 1307;
34. b) S. R. Stauffer, S. Lee, J. P. Stambuli, S. I. Hauck, J. F. Hartwig, Org. Lett. 2000, 2, 1423.
35. a) W. A. Herrmann, V. P. W. Böhm, C. W. K. Gstöttmayr, M. Grosche, C.-P. Reisinger, T. Weskamp, J. Organomet. Chem. 2001, 616, 617;
36. b) C. Yang, S. P. Nolan, Organometallics 2002, 21, 1020.
37. [2i]
38. For synthesis of 4f, see: W. A. Herrmann, L. J. Goossen, C. Köcher, G. R. J. Artus, Angew. Chem. Int. Ed. Engl. 1996, 35, 2805.
39. 1H NMR spectrum of the MPTA ester of 8b after derivatization of 2b by the procedure shown in Scheme 4.
40. a) For synthesis of 5a, see: F. Guillen, C. L. Winn, A. Alexakis, Tetrahedron: Asymmetry 2001, 12, 2083;
41. b) for synthesis of 5b, see: S. Lee, J. F. Hartwig, J. Org. Chem. 2001, 66, 3402;
42. c) for synthesis of 5c, see: T. J. Seiders, D. W. Ward, R. H. Grubbs, Org. Lett. 2001, 3, 3225;
43. [14c]
44. 1H-NMR spectrum of the MPTA ester of 8b derived from 2b.
45. 1H-NMR spectrum of the MPTA ester of 8a after derivatization of 2a by the procedure shown in Scheme 3.