Intramolecular Huisgen-type cyclization of platinum-bound pyrylium ions with alkenes and subsequent insertion into a benzylic C-H bond

Angewandte Chemie - International Edition

Volumn 47, Issue 39, 2008, Pages 7505-7507

  Oh, Chang Ho ^a   Lee, Ji Ho ^a   Lee, Su Jin ^a   Kim, Jae Il ^b   Hong, Chang Seop ^b  

^a Hanyang University   (South Korea)

^b Korea University   (South Korea)

Author keywords

Cyclization; Homogeneous catalysis; Insertion; Platinum; Pyrylium ions

Indexed keywords

CHEMICAL REACTIONS; CYCLIZATION; HYDROCARBONS; OLEFINS; PLATINUM;

BENZYLIC; C-H BONDS; C-H INSERTION; CARBENE COMPLEXES; CHEMICAL EQUATIONS; COMPLEX PRODUCTS; HOMOGENEOUS CATALYSIS; INSERTION; POLYCYCLIC COMPOUNDS; PYRYLIUM; PYRYLIUM IONS; RELATED PRODUCTS; SIDE CHAINS;

PLATINUM COMPOUNDS;

ALKENE; BENZENE; CARBENE; CARBON; DRUG DERIVATIVE; HYDROGEN; ION; METHANE; PLATINUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; X RAY CRYSTALLOGRAPHY;

ALKENES; BENZENE; CARBON; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HYDROGEN; IONS; METHANE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PLATINUM COMPOUNDS;

EID: 54749154384     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802425     Document Type: Article

References (29)

1. a) M. B. Fraga, Nat. Prod. Rep. 2005, 22, 465;
2. b) D. G. I. Kingston, H. Yuan, P. G. Jagtap, L. Samala in The Chemistry of Organic Natural Products, Vol. 84 (Eds.: W. Herz, G. W. Kirby, R. E. Moore, W. Steglich, C. Tamm), Springer, New York, 2002;
3. c) E. Baloglu, D. G. I. Kingston, J. Nat. Prod. 1999, 62, 1448.
4. a) B. Trillo, F. López, M. Gulías, L. Castedo, J. L. Mascareñas, Angew. Chem. 2008, 120, 965;
5. Angew. Chem. Int. Ed. 2008, 47, 951;
6. b) M. A. Battiste, P. M. Pelphrey, D. L. Wright, Chem. Eur. J. 2006, 12, 3438;
7. c) P. A. Wender, F. C. Bi, N. Buschmann, F. Gosselin, C. Kan, J.-M. Kee, H. Ohmura, Org. Lett. 2006, 8, 5373;
8. d) B. M. Trost, Y. Hu, D. B. Horne, J. Am. Chem. Soc. 2007, 129, 11781.
9. a) S. Shin, A. K. Gupta, C. Y. Rhim, C. H. Oh, Chem. Commun. 2005, 4429;
10. for the Huisgen [3+2] cycloaddition, see: b) R. Huisgen, Angew. Chem. 1968, 80, 329;
11. Angew. Chem. Int. Ed. Engl. 1968, 7, 321;
12. c) H. Hamberger, R. Huisgen, J. Chem. Soc. D 1971, 1190;
13. for a recent Pt-catalyzed benzannulation reaction, see: d) D. Hildebrandt, W. Huggenberg, M. Kanthak, T. Ploger, I. M. Muller, G. Dyker, Chem. Commun. 2006, 2260;
14. e) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814;
15. f) N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650;
16. g) N. Asao, H. Aikawa, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 7458;
17. h) H. Kusama, H. Funami, M. Shido, Y. Hara, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 2709;
18. i) H. Kusama, H. Funami, J. Takaya, N. Iwasawa, Org. Lett. 2004, 6, 605.
19. a) N. Kim, Y. Kim, W. Park, D. Sung, A. K. Gupta, C. H. Oh, Org. Lett. 2005, 7, 5289;
20. b) C. H. Oh, J. H. Ryu, H. I. Lee, Synlett 2007, 2337.
21. a) D. Seyferth, V. A. Mai, M. E. Gordon, J. Org. Chem. 1970, 35, 1993;
22. b) J. Adams, M. A. Poupart, L. Grenier, C. Schaller, N. Ouimet, R. Frenette, Tetrahedron Lett. 1989, 30, 1749.
23. a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467;
24. b) K. R. Roesch, R. C. Larock, J. Org. Chem. 2002, 67, 86-94.
25. 13C NMR spectroscopy and HRMS, and further supported by the X-ray crystal structure of 6g. The structure of 3a was confirmed further by chemical transformations.
26. H. Kusama, H. Funami, N. Iwasawa, Synthesis 2007, 2014.
27. 3/N,N-dimethylformamide, see: a) S. K. Mal, D. Ray, J. K. Ray, Tetrahedron Lett. 2004, 45, 277;
28. b) K. R. Buszek, Y. Jeong, Synth. Commun. 1994, 24, 2461.
29. CCDC 697658 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).