Rate and mechanism of the reaction of alkenes with aryl palladium complexes ligated by a bidentate P,P ligand in heck reactions

Chemistry - A European Journal

Volumn 13, Issue 7, 2007, Pages 2002-2011

  Amatore, Christian ^a   Godin, Béatrice ^a   Jutand, Anny ^a   Lemaître, Frédéric ^a  

^a CNRS   (France)

Author keywords

Heck reaction; Kinetics; P ligands; Palladium; Regioselectivity

Indexed keywords

COMPLEXATION; LIGANDS; OXIDATION; PALLADIUM COMPOUNDS; REACTION KINETICS; REGIOSELECTIVITY;

HECK REACTIONS; IODIDE IONS; OXIDATIVE ADDITION; P LIGANDS;

OLEFINS;

EID: 34047255523     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600153     Document Type: Article

References (48)

1. For reviews on Heck reactions see: a) A. de Mejeire, F. E. Meyer. Angew. Chem. 1994, 106, 2473-2506;
2. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411:
3. b) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2-7;
4. c) M. Shibasaki, E.M. Vogl, J. Organomet. Chem. 1999, 576, 1-15:
5. d) I. P. Beletskata, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066;
6. e) M. Larhed, A. Hallberg, Handbook of Organopalladiuin Chemistry for Organic Synthesis, Vol. I (Ed.: E. Negishi). Wiley-Interscience. New York, 2002, pp. 1133-1178.
7. 2 and dppp see: a) W. Cabri, I. Candiani, S. DeBernardinis, F. Francalanci, S. Penco, R. Santi, J. Org. Chem. 1991, 56, 5796-5800:
8. b) W. Cabri, I. Candiani, A. Bedeshi, R. Santi, Tetrahedron Lett. 1991, 32, 1753-1756:
9. c) W. Cabri, I. Candiani, A. Bedeshi, S. Penco, R. Santi. J. Org. Chem. 1992, 57, 1481-1486:
10. d) W. Cabri, I. Candiani, A. Bedeshi, R. Santi, J. Org. Chem. 1992, 57, 3558-3563:
11. e) W. A. Herrmann, C. Brossmer, K. Öfelc, M. Beller, H. Fisher, J. Mol. Catal. A 1995, 103, 133-146;
12. f) M. Larhed, A. Hallberg, J. Org. Chem. 1996, 61, 9582-9584:
13. g) M. Larhed, A. Hallberg, J. Org. Chem. 1997, 62, 7858-7862;
14. h) K. S. A. Vallin, M. Larhed, K. Johansson, A. Hallberg, J. Org. Chem. 2000, 65, 4537-4542;
15. i) M. Qadir, T. Möchel, K. K. Hii. Tetra hedron 2000, 56, 7975-7979:
16. j) K. S. A. Vallin, M. Larhed, A. Hallberg, J. Org. Chem. 2001, 66, 4340-4343;
17. k) K. S. A. Vallin, Q. S. Zhang, M. Larhed, D. P. Curran, A. Hallberg, J. Org. Chem. 2003, 68, 6639-6645.
18. a) L. E. Overman, D. J. Poon, Angew. Chem. 1997, 109, 536-538:
19. Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521:
20. b) A. Ashimori, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6488-6499.
21. a) F. Ozawa, A. Kubo, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 1417-1419:
22. b) T. Hayashi, A. Kubo, F. Ozawa, Pure Appl. Chem. 1992, 64, 421-427:
23. c) F. Ozawa, A. Kubo, Y. Matsumoto, T. Hayashi, Organometallics 1993, 12, 4188-4196.
24. a) K. Karabelas, C. Westerlund, A. Hallberg, J. Org. Chem. 1985, 50, 3896-3900:
25. b) R. Grigg, V. Loganathan, V. Santhakumar, A. Teasdale. Tetrahedron Lett. 1991, 32, 687-690.
26. Milstein et al. have established that the cationic complex was the reactive species generated from a neutral [Pd(dippp)ClPh] complex (dippp=1,3-bis(diisopropylphosphino)propane). M. Portnoy. Y. Ben-David, I. Rousso, D. Milstein. Organometallics 1994, 13, 3465-3479.
27. a) J. M. Brown, K. K. Hii, Angew. Chem. 1996, 108, 679-682:
28. Angew. Chem. Int. Ed. Engl. 1996, 35, 657-659:
29. b) K. K. Hii, T. D. W. Claridge, J. M. Brown. Angew. Chem. 1997, 109, 1033-1036;
30. Angew. Chem. Int. Ed. Engl. 1997, 36, 984-987;
31. c) R. J. Deeth, A. Smith, K. K. Hii, J. M. Brown. Tetrahedron Lett. 1998, 39, 3229-3232:
32. d) K. K. Hii, T. D. W. Claridge, R. Giernoth, J. M. Brown, Adv. Synth. Catal. 2004, 346, 983-988.
33. M. Ludwig, S. Strömberg. M. Svensson. B. Åkermark. Organometallics 1999, 18, 970-975.
34. For a theoretical approach to the regiochemistry of palladium-phosphine- catalyzed Heck reactions see: R. J. Deeth, A. Smith, J. M. Brown, J. Am. Chem. Soc. 2004, 126, 7144-7151.
35. a) C. Amatore, A. Jutand, A. Thuilliez, Organometallics 2001, 20, 3241-3249; For similar reactions involving the binap ligand see:
36. b) F. Ozawa, A. Kubo, T. Hayashi, Chem. Lett. 1992, 2177-2180.
37. S. Kozuch, S. Shaik, A. Jutand, C. Amatore, Chem. Eur. J. 2004, 10, 3072-3080.
38. 2IPh];
39. b) C. Amatore, E. Carré, A. Jutand, M. A. M'Barki, G. Meyer, Organometallics 1995, 14, 5605-5614.
40. C. Amatore, E. Carré, A. Jutand. Acta Chem. Scand. B 1998, 52, 100-106.
41. A.J. Bard, L. R. Faulkner, Electrochemical Methods, Wiley. New York. 1980. p. 136.
42. 2IPh] complexes, which are not electrochemically oxidized, the complexes [Pd(P,P)IPh] (P.P = bidentate bisphosphine ligand) are indeed oxidized. See: C. Amatore, G. Broeker, A. Jutand, F. Khalil, J. Am. Chem. Soc. 1997, 119, 5176-5185.
43. 2Me] was not fulfilled over the range of available methyl acrylate concentrations.
44. 0. this equality imposes the condition that at least 2500 equivalents of styrene (≈s30M) would he required to observe the saturation effect.
45. 4 (0.26M).
46. 2=CHRl, namely, exactly in the range observed for line A in Figure 4a.
47. a) L. J. Xu, W. P. Chen, J. Ross, J. L. Xiao, Org. Lett. 2001, 3, 295-297:
48. b) J. Mo, L. Xu, J. Xiao, J. Am. Chem. Soc. 2005, 127, 751-760