A carbocyclic carbene as an efficient catalyst ligand for C-C coupling reactions

Angewandte Chemie - International Edition

Volumn 45, Issue 23, 2006, Pages 3859-3862

  Herrmann, Wolfgang A ^a   Öfele, Karl ^a   Schneider, Sabine K ^a   Herdtweck, Eberhardt ^a   Hoffmann, Stephan D ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

C C coupling; Carbenes; Carbocycles; Homogeneous catalysis; Palladium

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; COMPLEXATION; PALLADIUM; THERMODYNAMIC STABILITY;

C-C COUPLING; CARBENES; CARBOCYCLES; HOMOGENEOUS CATALYSIS;

CATALYST ACTIVITY;

EID: 33746217438     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503589     Document Type: Article

References (28)

1. a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602;
2. Angew. Chem. Int. Ed. Engl. 1995, 34, 2371;
3. b) W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256;
4. Angew. Chem. Int. Ed. Engl. 1997, 36, 2162;
5. c) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39.
6. Review article : a) W. A. Herrmann, Angew. Chem. 2002, 114, 1342;
7. Angew. Chem. Int. Ed. 2002, 41, 1290;
8. b) W. A. Herrmann, T. Weskamp, V. P. W. Böhm, Adv. Organomet. Chem. 2002, 48, 1.
9. [1a] in 1995 more than 200 original publications from 15 research groups have appeared.
10. a) W. A. Herrmann, J. Fischer, M. Elison, C. Köcher, K. Öfele (Hoechst AG), DE 4447066.5A1, 1996, EP 0721953A1, 1996 [Chem. Abstr. 1996, 125, 143019y];
11. b) W. A. Herrmann, J. Fischer, M. Elison, C. Köcher (Hoechst AG), DE 4447068.1A1, 1996, EP 0719758A1, 1996, US 5.703.269, 1997 [Chem. Abstr. 1996, 125, 167571y];
12. c) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher (Celanese GmbH), DE 4447067.3A1, 1996, EP 0719753A1, 1995 [Chem. Abstr. 1996, 125, 167338c];
13. d) W. A. Herrmann (Hoechst AG), DE 4447070.3A1, 1996, EP 0721951A1, 1996 [Chem. Abstr. 1996, 125, 143016v];
14. e) W. A. Herrmann, C. Köcher, L. Goossen (Hoechst AG), DE 1961090.8A1, 1997, EP 888308, 1997, WO 9734875, 1997 [Chem. Abstr. 1997, 127, 318962v];
15. f) W. A. Herrmann, H.-C. Militzer, U. Scholz, C. Gstöttmayr (Bayer AG), EP 1308157A1, 2003.
16. -3). Smaller extinction effects were corrected with SHELXL-97 (G. M. Sheldrick, SHELXL-97, Program for Refinement of Crystal Structures, Universität Göttingen, 1997) [ε = 0.013(2)]. The molecule lies on an inversion center. The resulting partial disorder [0.830(4):0.170(4)]of the chlorine atoms C12/C13 was observed and resolved. CCDC-683874 contains the detailed crystallographic data for this publication. The data may be obtained free of charge from the Cambridge Crystallographic Data Centre under www.ccdc.cam.ac.uk/data_request/cif.
17. o)], wR2 = 0.0555 [all data], GOF = 1.116, shift/error ratio < 0.001. CCDC-603873 contains the detailed crystallographic data for this publication. The data may be obtained free of charge from the Cambridge Crystallographic Data Centre under www.ccdc.cam.ac.uk/data_request/cif.
18. a) N. T. Allison, Y. Kawada, W. M. Jones, J. Am. Chem. Soc. 1978, 100, 5224;
19. b) P. E. Riley, R. E. Davis, N. T. Allison, W. M. Jones, Inorg. Chem. 1982, 21, 1321.
20. a) Z. Lu, K. A. Abboud, W. M. Jones, J. Am. Chem. Soc. 1992, 114, 10991;
21. b) Z. Lu, W. M. Jones, W. R. Winchester, Organometallics 1993, 12, 1344.
22. Current literature, e.g. a) W. A. Herrmann, K. Öfele, D. von Preysing, S. K. Schneider, J. Organomet. Chem. 2003, 687, 229;
23. b) W. A. Herrmann in Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed. (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2002, p. 591-598;
24. W. A. Herrmann in Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed. (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2002, p. 775-793;
25. W. A. Herrmann in Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed. (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2002, p. 822-828.
26. W. A. Herrmann, V. P. W. Böhm, C. W. K. Gstöttmayer, M. Grosche, C.-P. Reisinger, T. Weskamp, J. Organomet. Chem. 2001, 617-618, 616.
27. G. A. Grasa, M. S. Viciu, J. Huang, C. Zhang, M. L. Trudell, S. P. Nolan, Organometallics, 2002, 21, 2866.
28. A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 6989.