Divergent insertion reactions of Pt-carbenes generated from [3+2] cyclization of platinum-bound pyrylliums

Chemistry - A European Journal

Volumn 15, Issue 1, 2009, Pages 71-74

  Oh, Chang Ho ^a   Lee, Ji Ho ^a   Lee, Sung Min ^a   Yi, Hyun Jik ^a   Hong, Chang Seop ^b  

^a Hanyang University   (South Korea)

^b Korea University   (South Korea)

Author keywords

Asymmetric catalysis; Carbenes; Cyclization; Insertion; Platinum

Indexed keywords

ARGON; CATALYSIS; CHEMICAL REACTIONS; CYCLIZATION; INERT GASES; PLATINUM; PROPANE; TOLUENE;

ARGON ATMOSPHERES; ASYMMETRIC CATALYSIS; C-H BONDS; CARBENE COMPLEXES; CARBENES; INSERTION; INSERTION REACTIONS; REACTION MIXTURES; TEST TUBES;

PLATINUM COMPOUNDS;

EID: 58449131542     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801887     Document Type: Article

References (46)

1. a) B. Trillo, F. López, M. Gulías, L. Castedo, J. L. Mascareňas, Angew. Chem. 2008, 120, 965;
2. Angew. Chem. Int. Ed. 2008, 47, 951;
3. b) M. A. Baltiste, P. M. Pelphrey, D. L. Wright, Chem. Eur. J. 2006, 12, 3438;
4. c) B. M. Trost, Y. Hu, D. B. Horne, J. Am. Chem. Soc. 2007, 129, 11781;
5. d) P. Liu, P. H.-Y. Cheong, Z.-X. Yu, P. A. Wender, K. N. Houk, Angew. Chem. 2008, 120, 4003;
6. Angew. Chem. Int. Ed. 2008, 47, 3939;
7. e) E. C. Garnier, L. S. Liebeskind, J. Am. Chem. Soc. 2008, 130, 7449;
8. f) R. D. Witherell K. E. O. Ylijoki, J. M. Stryker, J. Am. Chem. Soc. 2008, 130, 2176;
9. g) B. L. Ashfeld, K. A. Miller, A. J. Smith, K. Tran, S. F. Martin, J. Org. Chem. 2007, 72, 9018;
10. h) F. J. Gómez N. E. Kamber N. M. Deschamps, A. P. Cole, P. A. Wender, R. M. Waymouth, Organometallics 2007, 26, 4541;
11. i) A. Sailo, T. Ono, Y. Hanzawa, J. Org. Chem. 2006, 71, 6437;
12. j) P. A. Wender, L. O. Hausledt, J. Lim, J. A. Love, T. J. Williams, J.-Y. Yoon, J. Am. Chem. Soc. 2006, 128, 6302.
13. a) B. M. Fraga. Nat. Prod. Rep. 2005, 22, 465;
14. b) E. Baloglu, D. G. I. Kingston, J. Nat. Prod. 1999, 62, 1448.
15. C. H. Oh, J. H. Lee, S. J. Lee. J. I. Kim, C. S. Hong. Angew. Chem. 2008, 120, 7615;
16. Angew. Chem. Int. Ed. 2008, 47, 7505.
17. a) R. Huisgen, Angew. Chem. 1968, 80, 329;
18. Angew. Chem. Int. Ed. Engl. 1968, 7, 321;
19. b) H. Hamberger. R. Huisgen, J. Chem. Soc. D 1971, 1190.
20. N. Kim, Y. Kim, W. Park, D. Sung, A. K. Gupta, C. H. Oh, Org. Lett. 2005, 7, 5289.
21. For Rh-calalyzed annulations, see: S. Shin, A. K. Gupta, C. Y. Rhim, C. H. Oh, Chem. Commun. 2005, 4429.
22. For benzannulation of o-alkynylbenzaldehydes, see: a) N. Asao, H. Aikawa, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 7458;
23. b) N. Asao, K. Sato, Menggenbateer, Y. Yamamoto, J. Org. Chem. 2005, 70, 3682;
24. c) A. S. K. Hashmi, T. M. Frost, J, W. Bats, J. Am. Chem. Soc. 2000, 122, 11553;
25. d) J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809.
26. C. H. Oh, J. H. Ryu, H. I. Lee, Synlett 2007, 2337.
27. M. S. Ali, M. K. Pervez, M. Saleem, F. Ahmed, Nat Prod. Res. 2003, 17, 301.
28. a) H. Kusama, K. Ishida, H. Funami, N. Iwasawa, Angew. Chem. 2008, 120, 4981;
29. Angew. Chem. Int. Ed. 2008, 47, 4903;
30. b) H. Funami, H. Kusama, N. Iwasawa, Angew. Chem. 2007, 119, 927;
31. Angew. Chem. Int. Ed. 2007, 46, 909;
32. c) H. Kusama, H. Funami, M. Shido, Y. Hara, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 2709;
33. d) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814;
34. e) K. Miki, T. Yokoi, F. Nishino, Y. Kato, Y. Washitake, K. Ohe, S. Uemura, J. Org. Chem. 2004, 69, 1557.
35. All substrates 7 were easily prepared by known procedures a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467;
36. b) K. R. Roesch, R. C. Larock, J. Org. Chem. 2002, 67, 86.
37. a) Z. Geng, P. Yan, Y. Wang, X. Yao, Y. Han, J. Liang, J. Phys. Chem. A 2007, 111, 9961;
38. b) W. Shi, B. Zhang, J. Zhang, B. Liu, S. Zhang, J. Wang, Org. Lett. 2005, 7, 3103.
39. A. K. Ghosh, C. Ray, U. R. Ghatak, Tetrahedron Lett. 1992, 33, 655.
40. A. Kelecom, Tetrahedron 1983, 39, 3603.
41. a) T.-C. Lin, J.-M. Fang, Y.-S. Cheng, Phytochemistry 1999, 51, 793;
42. b) S. Hasegawa, T. Kojima, Y. Hirose, Phytochemistry 1985, 24, 1545;
43. c) S. Hasegawa, Y. Hirose, M. Yatagai, T. Takahashi, Chem. Lett. 1984, 1837.
44. C. M. Houlihan, C. T. Ho, S. S. Chang, J. Am. Oil Chem. Soc. 1984, 61, 1036.
45. X. A. Dominguez, V. H. Sanchez, G. S. Garcia, B. G. Espinosa, H. J. Williams, C. Ortiz, A. I. Scott, J. H. Reibenspies, J. Nat. Prod. 1992, 55, 221.
46. D. Hildebrandte, W. Hüggenberg, M. Kanthak, T. Plöger, I. M. Müller, G. Dyker, Chem. Commun. 2006, 2260.