Cationic NHC-Pd (NHC = N-heterocyclic carbene) complex-catalyzed cycloisomerization of dienes

Tetrahedron Letters

Volumn 48, Issue 35, 2007, Pages 6142-6146

  Song, Young Jin ^a   Jung, Il Gu ^b   Lee, Harim ^a   Lee, Young Tak ^b   Chung, Young Keun ^b   Jang, Hye Young ^a  

^a Ajou University   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 DIENE; ALKADIENE; CARBENOID; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; ISOMERIZATION; SYNTHESIS;

EID: 34547464719     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.162     Document Type: Article

References (53)

1. Trost B.M. Chem. Soc. Rev. 11 (1982) 141
2. Hudlicky T., and Price J.D. Chem. Rev. 89 (1989) 1467
3. Selected review articles related to the transition metal catalyzed cyclizations. Trost B.M. Acc. Chem. Res. 23 (1990) 34
4. Broene R.D., and Buchwald S. In: Hegedus L.S. (Ed). Comprehensive Organometallic Chemistry Vol. 12 (1995), Permagon, London 323
5. Ojima I., Tzamarioudaki M., Li Z., and Donovan R.J. Chem. Rev. 96 (1996) 635
6. Trost B.M., and Krische M.J. Synlett (1998) 1
7. Molander G.A., and Romero A.C. Chem. Rev. 102 (2002) 2161
8. Widenhoefer R.A. Acc. Chem. Res. 35 (2002) 905
9. Ikeda S.-I. Angew. Chem., Int. Ed. 42 (2003) 5120
10. Lloyd-Jones G.C. Org. Biomol. Chem. 1 (2003) 215
11. Jang H.-Y., and Krische M.J. Acc. Chem. Res. 37 (2004) 653
12. Piers W.E., Shapiro P.J., Bunel E.E., and Bercaw J.E. Synlett (1990) 74
13. Lehmkuhl H., and Tsien Y.L. Chem. Ber. 116 (1983) 2437
14. Okamoto S., and Livinghouse T. J. Am. Chem. Soc. 122 (2000) 1223
15. Christoffers J., and Bergman R.G. J. Am. Chem. Soc. 118 (1996) 4715
16. Bright A., Malone J.F., Nicholson J.K., Powell J., and Shaw B.L. J. Chem. Soc., Chem. Commun. (1971) 712
17. Grigg R., and Kongkathip B. J. Chem. Soc., Dalton. Trans. (1978) 333
18. Grigg R., Mitchell T.R.B., and Ramasubbu A. J. Chem. Soc., Chem. Commun. (1980) 27
19. Yamamoto Y., Ohkoshi N., Kameda M., and Itoh K. J. Org. Chem. 64 (1999) 2178
20. Yamamoto Y., Nakagai Y.-i., Ohkoshi N., and Itoh K. J. Am. Chem. Soc. 123 (2001) 6372
21. Terada Y., Arisawa M., and Nishida A. Angew. Chem., Int. Ed. 43 (2004) 4063
22. Radetich B., and RajanBabu T.V. J. Am. Chem. Soc. 120 (1998) 8007
23. RajanBabu T.V., Nomura N., Jin J., Radetich B., Park H., and Nandi M. Chem. Eur. J. 5 (1999) 1963
24. Böing C., Franciò G., and Leitner W. Adv. Synth. Catal. 347 (2005) 1537
25. Böing C., Franciò G., and Leitner W. Chem. Commun. (2005) 1456
26. Grigg R., Mitchell T.R.B., and Ramasubbu A. J. Chem. Soc., Chem. Commun. (1979) 669
27. Heumann A., and Moukhliss M. Synlett (1998) 1211
28. Widenhoefer R.A., and Perch N.S. Org. Lett. 1 (1999) 1103
29. Widenhoefer R.A. J. Am. Chem. Soc. 122 (2000) 10017
30. Bray K.L., Charmant J.P.H., Fairlamb I.J.S., and Lloyd-Jones G.C. Chem. Eur. J. 7 (2001) 4205
31. Kisanga P., Kisanga P., Goj L.A., and Widenhoefer R.A. J. Org. Chem. 66 (2001) 635
32. Goj L.A., and Widenhoefer R.A. J. Am. Chem. Soc. 123 (2001) 11133
33. Bray K.L., Fairlamb I.J.S., and Lloyd-Jones G.C. Chem. Commun. (2001) 187
34. Fairlamb I.J.S., Grant S., Whitwood A.C., Whitthall J., Batsanov A.S., and Collings J.C. J. Organomet. Chem. 690 (2005) 4462
35. Park S., Takeuchi D., and Osakada K. J. Am. Chem. Soc. 128 (2006) 3510
36. Goj L.A., Cisneros A., Yang W., and Widenhoefer R.A. J. Organomet. Chem. 687 (2003) 498
37. Kerber W.D., Koh J.H., and Gagné M.R. Org. Lett. 6 (2004) 3013
38. Huang I., Schanz H.-J., Stevens E.D., and Nolan S.P. Organometallics 18 (1999) 2370
39. Bourissou D., Guerret O., Gabbai{dotless}̈ F.P., and Bertrand G. Chem. Rev. 100 (2000) 39
40. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290
41. Garrison J.C., and Youngs W.J. Chem. Rev. 105 (2005) 3978
42. Sigman M.S., and Jensen D.R. Acc. Chem. Res. 39 (2006) 221
43. Prior to this report, (NHC)Pd catalyzed-cycloisomerization of bisdienes was published by Takacs. See Ref:. Takacs J.M., Venkataraman S., Andrew R.N., and Pelter L.S.W. J. Organomet. Chem. 690 (2005) 6205
44. Viciu M.S., Navarro O., Germaneau R.F., Kelly III R.A., Sommer W., Marion N., Stevens E.D., Cavallo L., and Nolan S.P. Organometallics 23 (2004) 1629
45. Marion N., Navarro O., Mei J., Stevens E.D., Scott N.M., and Nolan S.P. J. Am. Chem. Soc. 128 (2006) ; 4101
46. n: calcd: C, 69.70; H, 6.82; N, 3.87. Found: C, 69.88; H, 6.66; N, 3.80.
47. n: calcd: C, 70.01; H, 6.97; N, 3.80. Found: C, 70.46; H, 6.93; N, 3.56.
48. n: calcd: C, 53.67; H, 4.25; N, 3.58. Found: C, 53.48; H, 4.34; N, 3.26.
49. - catalyzed cycloisomerizations provide the product a at the initial stage. However, products b and c were also observed during the course of the reaction via Pd-catalyzed isomerization.
50. Reference for compound 2a. Oppolzer W., and Schröder F. Tetrahedron Lett. 35 (1994) 7939
51. -1.
52. Mecking S., and Keim W. Organometallics 15 (1996) 2650
53. Cao P., Wang B., and Zhang X. J. Am. Chem. Soc. 122 (2000) 6490