The Pd-catalyzed coupling of allyl halides and tin aryls: Why the catalytic reaction works and the stoichiometric reaction does not

Chemistry - A European Journal

Volumn 7, Issue 11, 2001, Pages 2481-2489

  Albéniz, Ana C ^a   Espinet, Pablo ^a   Martín Ruiz, Blanca ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Allyl ligands; Bridging aryls; C C coupling; Intermediates; Palladium; Reductive elimination

Indexed keywords

HALOGEN COMPOUNDS; OLEFINS; PALLADIUM; STOICHIOMETRY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

METAL COMPLEXES;

CATALYSIS;

ALKENE; ALLYL COMPOUND; BENZOQUINONE DERIVATIVE; HALIDE; PALLADIUM; TIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; DECOMPOSITION; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0035354661     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010601)7:11<2481::AID-CHEM24810>3.0.CO;2-2     Document Type: Article

References (57)

1. a) Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998;
2. b) V. Farina in Comprenhensive Organometallic Chemistry 11, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, 1995, Chapter 3.4.
3. a) V. Farina, V. Krishnamurthy, W. J. Scott, The Stille Reaction, Wiley, New York, 1998;
4. b) T. N. Mitchell, Synthesis 1992, 803-815;
5. c) J. K. Stille, Angew. Chem. 1986, 98, 504-519;
6. Angew. Chem. Int. Ed. Engl. 1986, 25, 508-523.
7. a) A. L. Casado, P. Espinet, J. Am. Chem. Soc. 1998, 120, 8978-8985,and references therein;
8. b) A. L. Casado, P. Espinet, A. M. Gallego, J. Am. Chem. Soc. 2000, 122, 11 771-11 782.
9. An interesting review that analyzes the elimination reactions involved in C-C bond formation has been published: J. M. Brown, N. A. Cooley, Chem. Rev. 1988, 88, 1031-1046.
10. A. Goliaszewski, J. Schwartz, Organometallics 1985, 4, 417-419.
11. A. Goliaszewski, J. Schwartz, J. Am. Chem. Soc. 1984, 106, 5028-5030.
12. J. S. Temple, M. Riediker, J. Schwartz, J. Am. Chem. Soc. 1982, 104, 1310-1315.
13. A. Goliaszewski, J. Schwartz, Tetrahedron Lett. 1985, 41, 5779-5789.
14. O. Kuhn, H. Mayr, Angew. Chem. 1999, 111, 356-358;
15. Angew. Chem. Int. Ed. 1999, 38, 343-346.
16. H. Kurosawa, S. Ogoshi, Bull. Chem. Soc. Jpn. 1998, 71, 973-984.
17. a) S. Numata, H. Kurosawa, J. Organomet. Chem. 1977, 131, 301-308.
18. b) H. Kurosawa, K. Shiba, K. Hirako, K. Kakiuchi, I. Ikeda, J. Chem. Soc. Chem. Commun. 1994, 1099-1100.
19. H. Kurosawa, M. Emoto, Y. Kawasaki, J. Organomet. Chent. 1988, 346, 137-146.
20. H. Kurosawa, M. Emoto, H. Ohnishi, K. Miki, N. Kasai, K. Tatsumi, A. Nakamura, J. Am. Chem. Soc. 1987, 109, 6333-6340.
21. H. Kurosawa, H. Kajimaru, M.-A. Miyoshi, H. Ohnishi, I. Ikeda, J. Mol. Catal. 1992, 74, 481-488.
22. R. Sutsman, J. Lau, M. Zipp, Tetrahedron Lett. 1986, 27, 5207-5210.
23. a) A. C. Albéniz, P. Espinet, Y.-S. Lin, J. Am. Chem. Soc. 1996, 118, 7145-7152;
24. b) A. C. Albéniz, P. Espinet, Y. Jeannin, M. Philoche-Levisalles, B. E. Mann, J. Am. Chem. Soc. 1990, 112, 6594-6600.
25. A. C. Albéniz, P. Espinet, C. Foces-Foces, F. H. Cano, Orgonometallics 1990, 9, 1079-1085.
26. R. Usón, J. Forniés, M. Tomás, J. M. Casas, Organometallics 1988, 7, 2279-2285.
27. a) P. Dierkes, S. Ramdeehul, L. Barloy, A. De Cian, J. Fischer, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3299-3301;
28. Angew. Chem. Int. Ed. 1998, 37, 3116-3118;
29. b) Y. Tsuji, T. Kusui, T. Kojima, Y. Sugiura, N. Yamada, S. Tanaka, M. Ebihara, T. Kawamura, Organometallics 1998, 17, 4835-4841;
30. c) S. Kudis, G. Helmchen, Angew. Chem. 1998, 110, 3210-3212;
31. Angew. Chem. Int. Ed. 1998, 37, 3047-3050;
32. d) H. Yang, M. A. Khan, K. M. Nicholas, Organometallics 1993, 12, 3485-3494;
33. e) R. C. Larock, H. Song, S. Kim, R. A. Jacobson, J. Chem. Soc. Chem. Commun. 1987, 834-836.
34. Cambridge Structural Database, CCDC, 12 Union Road, Cambridge CB21EZ, UK.
35. J. Emsley, The Elements, Clarendon Press, Oxford, 1991.
36. R. Usón, J. Forniés, M. Tomas, J. M. Casas, R. Navarro, J. Chem. Soc. Dalton Trans. 1989, 169-172.
37. a) P. W. N. M. Van Leeuwen, J. Lukas, A. P. Praat, M. Appelman, J. Organomet. Chem. 1972, 38, 199-207;
38. b) D. L. Tibbetts, T. L. Brown, J. Am. Chem. Soc. 1969, 91, 1108-1112.
39. N. D. Zelinsky, G. S. Pawlow, Ber. 1933, 66, 1420-1423.
40. We have previously reported examples of aryl exchange and hydride exchange in Pd complexes: a) A. C. Albéniz, P. Espinet, Y.-S. Lin, Organometallics 1997, 16, 4030-4032;
41. b) A. L. Casado, J. A. Casares, P. Espinet, Organometallics 1997, 16, 5730-5736 and references therein.
42. See, for example: a) U. Frey, L. Helm, A. E. Merbach, R. Romeo, J. Am. Chem. Soc. 1989, 111, 8161-8165, and references therein;
43. b) A. L. Casado, J. A. Casares, P. Espinet, Inorg. Chem. 1998, 37, 4154-4156;
44. c) A. C. Albéniz, A. L. Casado, P. Espinet, P. Inorg. Chem. 1999, 38, 2510-2515.
45. T. Yamamoto, A. Yamamoto, S. Ikeda, J. Am. Chem. Soc. 1971, 93, 3350-3359.
46. W. Lau, J. C. Huffman, J. K. Kochi, Organometallics 1982, 1, 155-169.
47. 0 strongly depends on the nature of the ligands bound to Pd and the solvent: H. Kurosawa, S. Ogoshi, Y. Kawasaki, S. Murai, M. Miyoshi, I. Ikeda, J. Am. Chem. Soc. 1990, 112, 2813-2814.
48. a) H. Grennberg, A. Gogoll, J.-E. Bäckvall, Organometallics 1993, 12, 1790-1793;
49. b) M. Hiramatsu, K. Shiozaki, T. Fujinami, S. Sakai, J. Organomet. Chem. 1983, 246, 203-211.
50. a) B. E. Mann, R. Pietropaolo, B. L. Shaw, J. Chem. Soc. Dalton Trans. 1973, 2390-2393;
51. b) F. R. Hartley, S. R. Jones, J. Organomet. Chem. 1974, 66, 465-473.
52. F. J. Arnaiz, Inorg. Synth. 1997, 31, 246-247.
53. M. A. Alonso, A. L. Casado, P. Espinet, J. M. Martínez-Ilarduya, C. Pérez-Briso, J. Organomet. Chem. 1998, 551, 9-20.
54. The data analysis and the drawing were performed with the programs: SMART V5.051, 1998;
55. SAINT V6.02, 1999;
56. G. M. Sheldrick, SHELXTL V5.1, 1998, Bruker AXS, Madison, Wi.
57. 1/2