Nonaqueous ionic liquids: Superior reaction media for the catalytic Heck-Vinylation of chloroarenes

Chemistry - A European Journal

Volumn 6, Issue 6, 2000, Pages 1017-1025

  Böhm, Volker P W ^a   Herrmann, Wolfgang A ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Alkenes; Arenes; Heck reaction; Nonaqueous ionic liquids; Palladium

Indexed keywords

ALKENE; CHLOROBENZENE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; STYRENE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0034677686     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000317)6:6<1017::AID-CHEM1017>3.0.CO;2-8     Document Type: Article

References (75)

1. a) T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581;
2. b) R. F. Heck, J. P. Nolley, J. Org. Chem. 1972, 37, 2320-2322.
3. Reviews: a) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985;
4. b) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl 1994, 33, 2379-2411;
5. b) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl 1994, 33, 2379-2411;
6. c) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 1995;
7. d) W. A. Herrmann in Applied Homogeneous Catalysis with Organometallic Compounds (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, pp. 712-726;
8. e) S. Bräse, A. de Meijere in Metal Catalyzed Cross Coupling Reactions (Eds.: P. J. Stang, F. Diederich), Wiley-VCH, Weinheim, 1997, pp. 99-166.
9. R. R. Bader, P. Baumeister, H.-U Blaser, Chimia 1996, 50, 99-105.
10. Reviews: a) V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047-1062;
11. b) T. H. Riermeier, A. Zapf, M. Beller, Top. Catal. 1998, 4, 301-305.
12. a) Y. Ben-David, M. Portnoy, M. Gozin, D. Milstein, Organometallics 1992, 11, 1995-1996;
13. b) M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734-4735.
14. a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602-2605; Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2374;
15. a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602-2605; Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2374;
16. b) W. A. Herrmann, C.-P. Reisinger, M. Spiegler, J. Organomet. Chem. 1998, 572, 93-96;
17. c) V. P. W. Böhm, T. Weskamp, W. A. Herrmann, unpublished results.
18. a) W. A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848;
19. a) W. A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848;
20. b) W. A. Herrmann, C. Broßmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357-1364;
21. c) W. A. Herrmann, V. P. W. Böhm, C.-P. Reisinger, J. Organomet. Chem. 1999, 576, 23-41.
22. M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687-11688.
23. a) J. B. Davison, N. M. Simon, S. A. Sojka, J. Mol. Catal. 1984, 22, 394-401;
24. b) A. Spencer, J. Organomet. Chem. 1984, 270, 115-120.
25. M. Beller, A. Zapf, Synlett 1998, 792-793.
26. M. Julia, M. Duteil, C. Grard, E. Kuntz, Bull. Soc. Chim. Fr. 1973, 2791-2794.
27. K. Kaneda, M. Higushi, T. Imanaka, J. Mol. Catal. 1990, 63, L33-L36.
28. a) M. T. Reetz, G. Lohmer, Chem. Commun. 1996, 1921-1922;
29. b) M. Beller, H. Fischer, K. Kühlein, C.-P. Reisinger, W. A. Herrmann, J. Organomet. Chem. 1996, 520, 257-259;
30. c) M. T. Reetz, R. Breinbauer, K. Wanninger, Tetrahedron Lett. 1996, 37, 4499-4502.
31. M. T. Reetz, G. Lohmer, R. Schwickardi, Angew. Chem. 1998, 110, 492-495; Angew. Chem. Int. Ed. 1998, 37, 481-483.
32. M. T. Reetz, G. Lohmer, R. Schwickardi, Angew. Chem. 1998, 110, 492-495; Angew. Chem. Int. Ed. 1998, 37, 481-483.
33. A. F. Littke, G. C. Fu, J. Org. Chem. 1999, 64, 10-11.
34. K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132.
35. a) W. J. Scott, J. Chem. Soc. Chem. Commun. 1987, 1755-1756;
36. b) J. F. Carpentier, F. Petit, A. Mortreux, V. Dufaud, J.-M. Basset, J. Thivolle-Cazat, J. Mol. Catal. 1993, 81, 1-15.
37. J. J. Bozell, C. E. Vogt, J. Am. Chem. Soc. 1988, 110, 2655.
38. a) T. Jeffery, J. Chem. Soc. Chem. Commun. 1984, 1287-1289;
39. b) T. Jeffery, Tetrahedron Lett. 1985, 26, 2667-2669.
40. a) Y. Chauvin, L. Mussmann, H. Olivier, Angew. Chem. 1995, 107, 2941-2943; Angew. Chem. Int. Ed. Engl. 1995, 34, 2698-2700;
41. a) Y. Chauvin, L. Mussmann, H. Olivier, Angew. Chem. 1995, 107, 2941-2943; Angew. Chem. Int. Ed. Engl. 1995, 34, 2698-2700;
42. b) C. L. Hussey, R. Quigley, K. R. Seddon, Inorg. Chem. 1995, 34, 370-380;
43. c) T. Welton, Chem. Rev. 1999, 99, 2071-2084.
44. D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 11, 1091-1092.
45. a) W. A. Herrmann, V. P. W. Böhm, J. Organomet. Chem. 1999, 572, 141-145;
46. b) V. P. W. Böhm, XXXIIth Jahrestreffen deutscher Katalytiker, Friedrichroda, Germany, 17-19 March 1999, P 59.
47. a) M. Huser, M.-T. Youinou, J. A. Osborn, Angew. Chem. 1989, 101, 1427-1430; Angew. Chem. Int. Ed. Engl. 1989, 28, 1386-1388;
48. a) M. Huser, M.-T. Youinou, J. A. Osborn, Angew. Chem. 1989, 101, 1427-1430; Angew. Chem. Int. Ed. Engl. 1989, 28, 1386-1388;
49. b) W. A. Herrmann, C. Broßmer, T. Priermeier, K. Öfele, J. Organomet. Chem. 1994, 481, 97-108.
50. A. W. Hofmann, Justus Liebigs Ann. Chem. 1851, 78, 253-286.
51. M. G. Gardiner, W. A. Herrmann, C.-P. Reisinger, J. Schwarz, M. Spiegler, J. Organomet. Chem. 1999, 572, 239-247.
52. T. Weskamp, V. P. W. Böhm, W. A. Herrmann, J. Organomet. Chem. 1999, 585, 348-352.
53. D. A. Albison, R. B. Bedford, P. N. Scully, Tetrahedron Lett. 1998, 39, 9793-9796.
54. J. Schwarz, V. P. W. Böhm, M. G. Gardiner, M. Grosche, W. A. Herrmann, W. Hieringer, G. Raudaschl-Sieber, Chem. Eur. J. 2000, 6, in press.
55. M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Veizijl, J. G. de Vries, Angew. Chem. 1998, 110, 688-690; Angew. Chem. Int. Ed. 1998, 37, 662-664.
56. M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Veizijl, J. G. de Vries, Angew. Chem. 1998, 110, 688-690; Angew. Chem. Int. Ed. 1998, 37, 662-664.
57. a) C.-M. Andersson, A. Hallberg, J. Org. Chem. 1987, 52, 3529-3536.
58. b) G. D. Daves, A. Hallberg, Chem. Rev. 1989, 89, 1433-1445.
59. a) T. Jeffery, Tetrahedron Lett. 1994, 35, 3051-3054;
60. b) T. Jeffery, Tetrahedron. 1996, 52, 10113-10130.
61. C. Amatore, E. Carré, A. Jutand, M. A. M'Barki, G. Meyer, Organometallics 1995, 14, 5605-5614.
62. B. L. Shaw, New J. Chem. 1998, 77-79.
63. H. Bönnemann, R. Brinkmann, R. Köppler, P. Neiteler, J. Richter, Adv. Mater. 1992, 4, 804-806.
64. W. A. Herrmann, C.-P. Reisinger, unpublished results.
65. a) C. Amatore, A. Jutand, M. A. M'Barki, Organometallics 1992, 11, 3009-3013;
66. b) F. Ozawa, A. Kubo, T. Hayashi, Chem. Lett. 1992, 2177-2180.
67. S. Klingelhöfer, W. Heitz, A. Greiner, S. Oestreich, S. Förster, M. Antonietti, J. Am. Chem. Soc. 1997, 119, 10116-10120.
68. B. J. Wakefield, Organomagnesium Methods in Organic Synthesis, Academic Press, London, 1995, p. 222.
69. T. Ukai, H. Kawazura, Y. Ishii, J. Organomet. Chem. 1974, 65, 253-266.
70. W. A. Herrmann, C.-P. Reisinger, K. Öfele, C. Broßmer, M. Beller, H. Fischer, J. Mol. Catal. A 1996, 108, 51-56.
71. L. S. Hegedus in Organometallic Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, p. 448.
72. W. A. Herrmann, J. Schwarz, M. G. Gardiner, Organometallics 1999, 18, 4082-4089.
73. W. P. Fehlhammer, W. A. Herrmann, K. Öfele in Handbuch der Präparativen Anorganischen Chemie, Vol. 3 (Ed.: G. Brauer), 3rd ed., Ferdinand Enke Verlag, Stuttgart, 1992, p. 2013.
74. M. Matsumoto, H. Yoshioko, K. Nakatsu, T. Yoshida, S. Otsuka, J. Am. Chem. Soc. 1974, 96, 3322-3324.
75. A. M. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518-1520.