Nonaqueous Ionic Liquids
1017±1025
de Meijere in Metal Catalyzed Cross Coupling Reactions (Eds.: P. J.
Stang, F. Diederich), Wiley-VCH, Weinheim, 1997, pp. 99 ± 166.
[3] R. R. Bader, P. Baumeister, H.-U. Blaser, Chimia 1996, 50, 99 ± 105.
[4] Reviews: a) V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047 ± 1062;
b) T. H. Riermeier, A. Zapf, M. Beller, Top. Catal. 1998, 4, 301 ± 305.
[5] a) Y. Ben-David, M. Portnoy, M. Gozin, D. Milstein, Organometallics
1992, 11, 1995 ± 1996; b) M. Portnoy, Y. Ben-David, D. Milstein,
Organometallics 1993, 12, 4734 ± 4735.
[6] 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; b) W. A. Herrmann, C.-P. Reisinger, M.
Spiegler, J. Organomet. Chem. 1998, 572, 93 ± 96; c) V. P. W. Böhm,
T. Weskamp, W. A. Herrmann, unpublished results.
[7] a) W. A. Herrmann, C. Broûmer, 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; b) W. A.
Herrmann, C. Broûmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M.
Beller, Chem. Eur. J. 1997, 3, 1357 ± 1364; c) W. A. Herrmann, V. P. W.
Böhm, C.-P. Reisinger, J. Organomet. Chem. 1999, 576, 23 ± 41.
[8] M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc.
1997, 119, 11687 ± 11688.
[23] a) M. Huser, M.-T. Youinou, J. A. Osborn, Angew. Chem. 1989, 101,
1427 ± 1430; Angew. Chem. Int. Ed. Engl. 1989, 28, 1386 ± 1388;
b) W. A. Herrmann, C. Broûmer, T. Priermeier, K. Öfele, J. Organo-
met. Chem. 1994, 481, 97 ± 108.
[24] A. W. Hofmann, Justus Liebigs Ann. Chem. 1851, 78, 253 ± 286.
[25] M. G. Gardiner, W. A. Herrmann, C.-P. Reisinger, J. Schwarz, M.
Spiegler, J. Organomet. Chem. 1999, 572, 239 ± 247.
[26] T. Weskamp, V. P. W. Böhm, W. A. Herrmann, J. Organomet. Chem.
1999, 585, 348 ± 352.
[27] D. A. Albison, R. B. Bedford, P. N. Scully, Tetrahedron Lett. 1998, 39,
9793 ± 9796.
[28] 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.
[29] M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl, J. G. de Vries,
Angew. Chem. 1998, 110, 688 ± 690; Angew. Chem. Int. Ed. 1998, 37,
662 ± 664.
[30] a) C.-M. Andersson, A. Hallberg, J. Org. Chem. 1987, 52, 3529 ± 3536.
b) G. D. Daves, A. Hallberg, Chem. Rev. 1989, 89, 1433 ± 1445.
[31] a) T. Jeffery, Tetrahedron Lett. 1994, 35, 3051 ± 3054; b) T. Jeffery,
Tetrahedron. 1996, 52, 10113 ± 10130.
Â
[9] a) J. B. Davison, N. M. Simon, S. A. Sojka, J. Mol. Catal. 1984, 22,
394 ± 401; b) A. Spencer, J. Organomet. Chem. 1984, 270, 115 ± 120.
[10] M. Beller, A. Zapf, Synlett 1998, 792 ± 793.
[32] C. Amatore, E. Carre, A. Jutand, M. A. M'Barki, G. Meyer, Organo-
metallics 1995, 14, 5605 ± 5614.
[33] B. L. Shaw, New J. Chem. 1998, 77 ± 79.
[11] M. Julia, M. Duteil, C. Grard, E. Kuntz, Bull. Soc. Chim. Fr. 1973,
2791 ± 2794.
[34] H. Bönnemann, R. Brinkmann, R. Köppler, P. Neiteler, J. Richter,
Adv. Mater. 1992, 4, 804 ± 806.
[12] K. Kaneda, M. Higushi, T. Imanaka, J. Mol. Catal. 1990, 63, L33-L36.
[13] a) M. T. Reetz, G. Lohmer, Chem. Commun. 1996, 1921 ± 1922; b) M.
Beller, H. Fischer, K. Kühlein, C.-P. Reisinger, W. A. Herrmann, J.
Organomet. Chem. 1996, 520, 257 ± 259; c) M. T. Reetz, R. Brein-
bauer, K. Wanninger, Tetrahedron Lett. 1996, 37, 4499 ± 4502.
[14] M. T. Reetz, G. Lohmer, R. Schwickardi, Angew. Chem. 1998, 110,
492 ± 495; Angew. Chem. Int. Ed. 1998, 37, 481 ± 483.
[15] A. F. Littke, G. C. Fu, J. Org. Chem. 1999, 64, 10 ± 11.
[16] K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121,
2123 ± 2132.
[35] W. A. Herrmann, C.-P. Reisinger, unpublished results.
[36] a) C. Amatore, A. Jutand, M. A. MꢁBarki, Organometallics 1992, 11,
3009 ± 3013; b) F. Ozawa, A. Kubo, T. Hayashi, Chem. Lett. 1992,
2177 ± 2180.
[37] S. Klingelhöfer, W. Heitz, A. Greiner, S. Oestreich, S. Förster, M.
Antonietti, J. Am. Chem. Soc. 1997, 119, 10116 ± 10120.
[38] B. J. Wakefield, Organomagnesium Methods in Organic Synthesis,
Academic Press, London, 1995, p. 222.
[39] T. Ukai, H. Kawazura, Y. Ishii, J. Organomet. Chem. 1974, 65, 253 ±
266.
[17] a) W. J. Scott, J. Chem. Soc. Chem. Commun. 1987, 1755 ± 1756; b) J. F.
Carpentier, F. Petit, A. Mortreux, V. Dufaud, J.-M. Basset, J. Thivolle-
Cazat, J. Mol. Catal. 1993, 81, 1 ± 15.
[18] J. J. Bozell, C. E. Vogt, J. Am. Chem. Soc. 1988, 110, 2655.
[19] a) T. Jeffery, J. Chem. Soc. Chem. Commun. 1984, 1287 ± 1289; b) T.
Jeffery, Tetrahedron Lett. 1985, 26, 2667 ± 2669.
[40] W. A. Herrmann, C.-P. Reisinger, K. Öfele, C. Broûmer, M. Beller, H.
Fischer, J. Mol. Catal. A 1996, 108, 51 ± 56.
[41] L. S. Hegedus in Organometallic Synthesis (Ed.: M. Schlosser), Wiley,
Chichester, 1994, p. 448.
[42] W. A. Herrmann, J. Schwarz, M. G. Gardiner, Organometallics 1999,
18, 4082 ± 4089.
[20] a) Y. Chauvin, L. Mussmann, H. Olivier, Angew. Chem. 1995, 107,
2941 ± 2943; Angew. Chem. Int. Ed. Engl. 1995, 34, 2698 ± 2700;
b) C. L. Hussey, R. Quigley, K. R. Seddon, Inorg. Chem. 1995, 34,
370 ± 380; c) T. Welton, Chem. Rev. 1999, 99, 2071 ± 2084.
[21] D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 11, 1091 ±
1092.
[22] a) W. A. Herrmann, V. P. W. Böhm, J. Organomet. Chem. 1999, 572,
141 ± 145; b) V. P. W. Böhm, XXXIIth Jahrestreffen deutscher Kata-
lytiker, Friedrichroda, Germany, 17 ± 19 March 1999, P 59.
[43] 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.
[44] M. Matsumoto, H. Yoshioko, K. Nakatsu, T. Yoshida, S. Otsuka, J.
Am. Chem. Soc. 1974, 96, 3322 ± 3324.
[45] A. M. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J.
Timmers, Organometallics 1996, 15, 1518 ± 1520.
Received: June 30, 1999 [F 1881]
Chem. Eur. J. 2000, 6, No. 6
ꢀ WILEY-VCH Verlag GmbH, D-69451 Weinheim, 2000
0947-6539/00/0606-1025 $ 17.50+.50/0
1025