Palladium(0)-catalyzed cis-selective alkylative and arylative cyclization of alkynyl enones with organoboron reagents

Tetrahedron Letters

Volumn 49, Issue 26, 2008, Pages 4174-4177

  Tsukamoto, Hirokazu ^a   Suzuki, Takamichi ^a   Uchiyama, Tomomi ^a   Kondo, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; ALKYNE; ALKYNYL GROUP; BORON; FUNCTIONAL GROUP; NICKEL; ORGANOBORON DERIVATIVE; PALLADIUM; PHOSPHINE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; ELECTRON; PROTON TRANSPORT; STEREOCHEMISTRY;

TETRA;

EID: 43849100005     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.111     Document Type: Article

References (50)

1. Suzuki-Miyaura cross-coupling:. Miyaura N. In: Miyaura N. (Ed). Top. Curr. Chem. Vol. 219 (2002), Springer, New York 11-59
2. Diarylation of allenes and alkynes:. Huang T.-H., Chang H.-M., Wu M.-Y., and Cheng C.-H. J. Org. Chem. 67 (2002) 99-105
3. Zhou C., Emrich D.E., and Larock R.C. Org. Lett. 5 (2003) 1579-1582
4. Zhou C., and Larock R.C. J. Org. Chem. 70 (2005) 3765-3777
5. Hydroarylation of alkynes and allenes:. Oh C.H., Jung H.H., Kim K.S., and Kim N. Angew. Chem., Int. Ed. 42 (2003) 805-808
6. Kim N., Kim K.-S., Gupta A.K., and Oh C.H. Chem. Commun. (2004) 618-619
7. Oh C.H., Park S.J., Ryu J.H., and Gupta A.K. Tetrahedron Lett. 45 (2004) 7039-7042
8. Oh C.H., Ahn T.W., and Reddy V.R. Chem. Commun. (2003) 2622-2623
9. Ma S., Jiao N., and Ye L. Chem. Eur. J. 9 (2003) 6049-6056
10. Qian R., Guo H., Liao Y., Guo Y., and Ma S. Angew. Chem., Int. Ed. 42 (2005) 4771-4774
11. Ma S., Guo H., and Yu F. J. Org. Chem. 71 (2006) 6634-6636
12. Guo H., and Ma S. Synthesis (2007) 2731-2745
13. Arylation of allylic and propargylic alcohols:. Tsukamoto H., Sato M., and Kondo Y. Chem. Commun. (2004) 1200-1201
14. Kayaki Y., Koda T., and Ikariya T. Eur. J. Org. Chem. (2004) 4989-4993
15. Manabe K., Nakada K., Aoyama N., and Kobayashi S. Adv. Synth. Catal. 347 (2005) 1499-1503
16. Yoshida M., Gotou T., and Ihara M. Chem. Commun. (2004) 1124-1125
17. Yoshida M., Gotou T., and Ihara M. Tetrahedron Lett. 45 (2004) 5573-5575
18. Alkylative cyclization of alkyne- and allene-aldehydes:. Tsukamoto H., Ueno T., and Kondo Y. J. Am. Chem. Soc. 128 (2006) 1406-1407
19. Tsukamoto H., Ueno T., and Kondo Y. Org. Lett. 9 (2007) 3033-3036
20. Tsukamoto H., Matsumoto T., and Kondo Y. J. Am. Chem. Soc. 130 (2008) 388-389
21. Arylative cyclization of allene-aldehydes using reducing metals:. Ha Y.-H., and Kang S.-K. Org. Lett. 4 (2002) 1143-1146
22. Kang S.-K., Lee S.-W., Jung J., and Lim Y. J. Org. Chem. 67 (2002) 4376-4379
23. Arylative cyclization of other functionalized alkynes and allenes:. Zhu G., and Zhang Z. Org. Lett. 5 (2003) 3645-3648
24. Zhu G., and Zhang Z. Org. Lett. 6 (2004) 4041-4047
25. Wang F., Tong X., Cheng J., and Zhang Z. Chem. Eur. J. 10 (2004) 5338-5344
26. Gupta A.K., Rhim C.Y., and Oh C.H. Tetrahedron Lett. 46 (2005) 2247-2250
27. Oh C.H., Park D.I., Jung S.H., Reddy V.R., Gupta A.K., and Kim Y.M. Synlett (2005) 2092-2094
28. Oblinger E., and Montgomery J. J. Am. Chem. Soc. 119 (1997) 9065-9066
29. Ni Y., Amarasinghe K.K.D., and Montgomery J. Org. Lett. 4 (2002) 1743-1745
30. Ogoshi S., Arai T., Ohashi M., and Kurosawa H. Chem. Commun. (2008) 1347-1349
31. There is one example of the Pd-catalyzed cis-selective acylative cyclization of alkynyl enones and subsequent intramolecular aldol reaction with acylzirconocene chloride:. Hanzawa Y., Yabe M., Oka Y., and Taguchi T. Org. Lett. 4 (2002) 4061
32. Montgomery J., and Savchenko A.V. J. Am. Chem. Soc. 118 (1996) 2099-2100
33. Montgomery J., Seo J., and Chui H.M.P. Tetrahedron Lett. 37 (1996) 6839-6842
34. Montgomery J., Oblinger E., and Savchenko A.V. J. Am. Chem. Soc. 119 (1997) 4911-4920
35. Montgomery J., Chevliakov M.V., and Brielmann H.L. Tetrahedron 53 (1997) 16449-16462
36. Amarasinghe K.K.D., Chowdhury S.K., Heeg M.J., and Montgomery J. Organometallics 20 (2001) 370-372
37. Hratchian H.P., Chowdhury S.K., Gutiérrez-García V.M., Amarasinghe K.K.D., Heeg M.J., Schlegel H.B., and Montgomery J. Organometallics 23 (2004) 4636-4646
38. Herath A., Thompson B.B., and Montgomery J. J. Am. Chem. Soc. 129 (2007) 8712-8713
39. Commercially available arylboronic acids contain its boronic anhydrides.
40. 5 in the presence of an excess of phosphines:. Otsuka S., Yoshida T., Matsumoto M., and Nakatsu K. J. Am. Chem. Soc. 98 (1976) 5850-5858
41. 10a
42. 4 turned out to be effective for the cyclization of more reactive alkyne-enones such as 4g.
43. 0 occurs in the presence of strong Brønsted or Lewis acid:. Ogoshi S., Yoshida T., Nishida T., Morita M., and Kurosawa H. J. Am. Chem. Soc. 123 (2001) 1944-1950
44. Ogoshi S., Morita M., and Kurosawa H. J. Am. Chem. Soc. 125 (2003) 9020-9021 {A figure is presented}
45. 0-catalyzed reactions of alkynyl enone 4a as well as alkynyl aldehydes in the absence of nucleophiles gave no cyclized products.
46. Ruthenium and cobalt catalysts were also reported to form metallacycle with alkynyl enones. Trost B.M., Brown R.E., and Toste F.D. J. Am. Chem. Soc. 122 (2000) 5877
47. Chang H.-T., Jayanth T.T., Wang C.-C., and Cheng C.-H. J. Am. Chem. Soc. 129 (2007) 12032-12041
48. Shintani R., Tsurusaki A., Okamoto K., and Hayashi T. Angew. Chem., Int. Ed. 44 (2005) 3909-3912
49. Kressierer C.J., and Müller T.J.J. Angew. Chem., Int. Ed. 43 (2004) 5997-6000
50. Holzapfel C.W., and Marais L. Tetrahedron Lett. 39 (1998) 2179-2182