Copper-catalyzed synthesis of 1,3-butadienylphosphine oxides and chemoselective phosphoryl reduction to stereodefined 1,3-butadienylphosphines

Advanced Synthesis and Catalysis

Volumn 355, Issue 14-15, 2013, Pages 2822-2826

  Gatignol, Jérémie ^a   Alayrac, Carole ^a   Lohier, Jean François ^a   Ballester, Jorge ^b   Taillefer, Marc ^b   Gaumont, Annie Claude ^a  

^a UNIVERSITÉ DE CAEN   (France)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Butadienylphosphine oxides; Butadienylphosphines; C P coupling; Copper catalysis

Indexed keywords

EID: 84895107535     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300618     Document Type: Article

References (53)

1. Recent reviews: a) D. S. Surry, S. L. Buchwald, Chem. Sci. 2010, 1, 13;
2. F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 7088
3. Angew. Chem. Int. Ed. 2009, 48, 6954;
4. F. Monnier, M. Taillefer, Angew. Chem. 2008, 120, 3140
5. Angew. Chem. Int. Ed. 2008, 47, 3096;
6. G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054.
7. For a recent review on transition metal-catalyzed C-P cross-couplings, see: F. M. J. Tappe, V. T. Trepohl, M. Oestreich, Synthesis 2010, 3037.
8. For selected examples of phosphine oxides or phosphite derivatives as coupling partners in the aryl series, see: a) M. Stankevic, A. Wlodarczyk, Tetrahedron 2013, 69, 73;
9. R. Zhuang, J. Xu, Z. Cai, G. Tang, M. Fang, Y. Zhao, Org. Lett. 2011, 13, 2110;
10. M. Font, T. Parella, M. Costas, X. Ribas, Organometallics 2012, 31, 7976;
11. N. B. Karlstedt, I. P. Beletskaya, Russ. J. Org. Chem. 2011, 47, 1011;
12. N. T. McDougal, J. Streuff, H. Mukherjee, S. C. Virgil, B. M. Stoltz, Tetrahedron Lett. 2010, 51, 5550;
13. C. Huang, X. Tang, H. Fu, Y. Jiang, Y. Zhao, J. Org. Chem. 2006, 71, 5020.
14. For phosphines as coupling partners, see: a) D. Gelman, L. Jiang, S. L. Buchwald, Org. Lett. 2003, 5, 2315;
15. D. Van Allen, D. Venkataraman, J. Org. Chem. 2003, 68, 4590;
16. K. Tani, D. C. Behenna, R. M. McFadden, B. M. Stoltz, Org. Lett. 2007, 9, 2529.
17. For tandem phosphine oxide reduction and C-P crosscoupling, see: Y. Li, S. Das, S. Zhou, K. Junge, M. Beller, J. Am. Chem. Soc. 2012, 134, 9727.
18. a) J. Hu, N. Zhao, B. Yang, G. Wang, L.-N. Guo, Y.-M. Liang, S.-D. Yang, Chem. Eur. J. 2011, 17, 5516;
19. G. Evano, K. Tadiparthi, F. Couty, Chem. Commun. 2011, 47, 179;
20. S. Thielges, P. Bisseret, J. Eustache, Org. Lett. 2005, 7, 681;
21. H. Xu, S. Gu, W. Chen, D. Li, J. Dou, J. Org. Chem. 2011, 76, 2448.
22. For Cu- or Pd-catalyzed cross coupling reactions respectively, see for example: a) E. Bernoud, C. Alayrac, O. Delacroix, A.-C. Gaumont, Chem. Commun. 2011, 47, 3239;
23. D. Julienne, J.-F. Lohier, O. Delacroix, A.- C. Gaumont, J. Org. Chem. 2007, 72, 2247; for catalytic hydrophosphinations
24. B. Join, D. Mimeau, O. Delacroix, A.-C. Gaumont, Chem. Commun. 2006, 3249.
25. For nucleophilic additions onto vinylphosphine oxides, see for example: a) M. Stankevic, M. Jaklinska, K. M. Pietrusiewicz, J. Org. Chem. 2012, 77, 1991;
26. A. M. Gonzalez-Nogal, P. Cuadrado, M. A. Sarmentero, Tetrahedron 2010, 66, 9610
27. c) B. Bartels, J. Clayden, C. Gonzalez Martin, A. Nelson, M. G. Russell, S. Warren, J. Chem. Soc. Perkin Trans. 1 1999, 1807
28. d) D. J. Fox, J. A. Medlock, R. Vosser, S. Warren, J. Chem. Soc. Perkin Trans. 1 2001, 2240;
29. e) J. Clayden, A. Nelson, S. Warren, Tetrahedron Lett. 1997, 38, 3471.
30. For examples of hemilabile phosphine oxide ligands, see: a) V. V. Grushin, Chem. Rev. 2004, 104, 1629;
31. b) R. Weber, U. Englert, B. Ganter, W. Keim, M. Möthrath, Chem. Commun. 2000, 1419;
32. c) C. Abu-Gnim, I. Amer, J. Organomet. Chem. 1996, 516, 235.
33. a) F. Mathey, G. Muller, Can. J. Chem. 1978, 56, 2486, and references cited therein
34. b) K. M. Pietrusiewicz, M. Kuznikowski, M. Koprowski, Tetrahedron: Asymmetry 1993, 4, 2143
35. c) L.-B. Han, C.-Q. Zhao, M. Tanaka, J. Org. Chem. 2001, 66, 5929
36. d) C. L. Ma, X. Y. Lu, Y. X. Ma, Chin. Chem. Lett. 1995, 6, 747.
37. H. Kaddouri, V. Vicente, A. Ouali, F. Ouazzani, M. Taillefer, Angew. Chem. 2009, 121, 339
38. Angew. Chem. Int. Ed. 2009, 48, 333.
39. For the preparation of (E,E)-1-bromo-1,3-butadienes, see: a) E. J. Corey, P. L. Fuchs, Tetrahedron Lett. 1972, 13, 3769
40. b) S. Abbas, C. J. Hayes, S. Worden, Tetrahedron Lett. 2000, 41, 3215.
41. M. I. Kabachnik, T. Y. Medved, E. I. Matrosov, Dokl. Akad. Nauk SSSR 1965, 162, 339.
42. For the preparation of (Z,E)-2a, see: J. Uenishi, R. Kawahama, O. Yonemitsu, J. Tsuji, J. Org. Chem. 1998, 63, 8965.
43. a) D. Julienne, F. Toulgoat, O. Delacroix, A.-C. Gaumont, Curr. Org. Chem. 2010, 14, 1195
44. b) Homogeneous Catalysis, Understanding the Art, (Ed.: P. W. N. M. van Leeuwen), Kluwer Academic Publishers, Dordrecht, 2004
45. c) S. Ortial, D. A. Thompson, J.-L. Montchamp, J. Org. Chem. 2010, 75, 8166
46. d) S. Ortial, J.-L. Montchamp, Org. Lett. 2011, 13, 3134.
47. F. Mathey, F. Mercier, C. Santini, Inorg. Chem. 1980, 19, 1813.
48. D. Gloyna, H. G. Henning, Angew. Chem. 1966, 78, 907
49. Angew. Chem. Int. Ed. Engl. 1966, 5, 847.
50. For a comprehensive literature survey, see: K. V. Rajendran, D. G. Gilheany, Chem. Commun. 2012, 48, 817, and references cited therein.
51. Y. Li, L.-Q. Lu, S. Das, S. Pisiewicz, K. Junge, M. Beller, J. Am. Chem. Soc. 2012, 134, 18325.
52. J.-F. Pilard, G. Baba, A.-C. Gaumont, J.-M. Denis, Synlett 1995, 1168.
53. The reduction conditions reported during the course of this work and involving tetramethyldisiloxane (TMDS) as mild reducing agent (3 equiv.) in the presence of a catalytic amount of copper(II) triflate (10 mol%) in toluene at 100 °C as described in ref.[5] were tested on (E,E)-3a and afforded (E,E)-4a in 65% yield.