Palladium-catalyzed three-component 1:2:1 coupling of aryl iodides, alkynes, and alkenes to produce 1,3,5-hexatriene derivatives

Advanced Synthesis and Catalysis

Volumn 351, Issue 9, 2009, Pages 1431-1436

  Horiguchi, Hakaru ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C C coupling; Heck reaction; Multicomponent reactions; Oligoenes; Palladium

Indexed keywords

EID: 67549112089     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900096     Document Type: Article

References (45)

1. a) S. Bräse, A. de Meijere, in: Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1, (Ed. : E. Negishi), Wiley-Interscience, New York, 2002, pp 1369-1429;
2. b) J. Tsuji, Palladium Reagents and Catalysts, 2nd edn., John Wiley & Sons, Chichester, UK, 2004, pp 201-265;
3. c) S. Bräse, A. de Meijere, in: Metal-Catalyzed Cross-Coupling Reactions, Vol. 1, (Eds.: A. de Meijere, F Diederich), Wiley-VCH, Weinheim, 2004, pp 224-276;
4. d) G. Balme, D. Bouyssi, N. Monteiro, in: Multicomponent Reactions, (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005, pp 224276;
5. see also: E.-I. Negishi, Z. Huang, G. Wang, S. Mohan, C. Wang, H. Hattori, Acc. Chem. Res. 2008, 41, 1474.
6. For recent examples: a) Q. Huang, R. C. Larock, Org. Lett. 2002, 4, 2505;
7. b) Q. Huang, R. C. Larock, J. Org. Chem. 2003, 68, 7342;
8. c) C. J. Kressierer, T. J. J. Müller, Angew. Chem. 2004, 116, 6123;
9. Angew. Chem. Int. Ed. 2004, 43, 5997;
10. d) D. M. D'Souza, F Rominger, T. J. J. Müller, Angew. Chem. 2005, 117, 156;
11. Angew. Chem. Int. Ed. 2005, 44, 153;
12. e) C. Bour, J. Suffert, Org. Lett. 2005, 7, 653;
13. f) G. Zhu, X. Tong, J. Cheng, Y. Sun, D. Li, Z. Zhang, J. Org. Chem. 2005, 70, 1712;
14. g) W. S. Cheung, R. J. Patch, M. R. Player, J. Org. Chem. 2005, 70, 3741;
15. h) R. Yanada, S. Obika, T. Inokuma, K. Yanada, M. Yamashita, S. Ohta, Y. Takemoto, J. Org. Chem. 2005, 70, 6972.
16. Intermolecular reaction with organoboron reagents: a) A. N. Thadani, V. H. Rawal, Org. Lett. 2002, 4, 4317;
17. b) C. Zhou, D. E. Emrich, R. C. Larock, Org. Lett. 2003, 5, 1579;
18. c) X. Zhang, R. C. Larock, Org. Lett. 2003, 5, 2993;
19. d) C. Zhou, R. C. Larock, J. Org. Chem. 2005, 70, 3765.
20. Intermolecular reaction with terminal alkynes: a) M. Pal, K. Parasuraman, V Subramanian, R. Dakarapu, K. R. Yeleswarapu, Tetrahedron Lett. 2004, 45, 2305;
21. b) L. R. Pottier, J.-F. Peyrat, M. Alami, J.-D. Brion, Synlett 2004, 1503;
22. c) M. Shi, L.-P. Liu, J. Tang, Org. Lett. 2005, 7, 3085.
23. a) T. Satoh, S. Ogino, M. Miura, M. Nomura, Angew. Chem. 2004, 116, 5173;
24. Angew. Chem. Int. Ed. 2004, 43, 5063;
25. b) H. Horiguchi, H. Tsurugi, T Satoh, M. Miura, Adv. Synth. Catal. 2008, 350, 509.
26. Intermolecular reaction with alkenes: a) K. Shibata, T. Satoh, M. Miura, Org. Lett. 2005, 7, 1781;
27. b) K. Shibata, T. Satoh, M. Miura, Adv. Synth. Catal. 2007, 349, 2317;
28. c) T. Satoh, H. Tsurugi, M. Miura, Chem. Rec. 2008, 8, 326.
29. [6a] heterogeneously catalyzed- and rhodium-catalyzed versions of similar three-component couplings were reported: d) M. L. Kantam, P. Srinivas, K. B. Shiva Kumar, R. Irivedi, Catal. Commun. 2007, 8, 991;
30. e) T. Kurahashi, H. Shinokubo, A. Osuka, Angew. Chem. 2006, 118, 6484;
31. Angew. Chem. Int. Ed. 2006, 45, 6336.
32. S. Kawasaki, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 6836.
33. For recent papers: a) S. Hünig, M. Kemmer, H. Wenner, F. Barbosa, G. Gescheidt, I. F. Perepichka, P. Bäuerle, A. Emge, K. Peters, Chem. Eur. J. 2000, 6, 2618;
34. b) J.-H. Kim, S. Noh, K. Kim, S.-T. Lim, D.-M. Shin, Synth. Met. 2001, 117, 227;
35. c) T. Suzuki, H. Higu-chi, M. Ohkita, T. Tsuji, Chem. Commun. 2001, 1574;
36. d) U. Lawrentz, W. Grahn, K. Lukaszuk, C. Klein, R. Wortmann, A. Feldner, D. Scherer, Chem. Eur. J. 2002, 8, 1573;
37. e) R. Davis, V. A. Mallia, S. Das, Chem. Mater. 2003, 15, 1057;
38. f) J. L. Gage, H. A. Kirst, D. O'Neil, B. A. David, C. K. Smith II, S. A. Naylor, Bioorg. Med. Chem. 2003, 11, 4083;
39. g) A. P. Lightfoot, S. J. R. Twid-dle, A. Whiting, Org. Biomol. Chem. 2005, 3, 3167, and references cited therein.
40. CCDC 719988 contains the supplementary crystallography data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
41. G. Dyker, A. Kellner, Tetrahedron Lett. 1994, 35, 7633.
42. G. Wu, A. L. Rheingold, S. J. Gelb, R. F. Heck, Organometallics 1987, 6, 1941.
43. a) S. Chowdhury, S. Roy, J. Org. Chem. 1997, 62, 199;
44. b) J. Prakash Das, S. Roy, J. Org. Chem. 2002, 67, 7861.
45. M. J. Mio, L. C. Kopel, J. B. Braun, T.L. Gadzikwa, K. L. Hull, R. G. Brisbois, C.J. Markworth, P.A. Grieco, Org. Lett. 2002, 4, 3199.