Nickel-catalyzed cross-coupling of aryl chlorides with aryl Grignard reagents

Angewandte Chemie - International Edition

Volumn 39, Issue 9, 2000, Pages 1602-1604

  Böhm, Volker P W ^a   Weskamp, Thomas ^a,b   Gstöttmayr, Christian W K ^a   Herrmann, Wolfgang A ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b SYMYX TECHNOLOGIES   (United States)

Author keywords

C C coupling; Combinatorial chemistry; Homogeneous catalysis; N heterocycles; Nickel

Indexed keywords

CHLORIDE; NICKEL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENVIRONMENTAL TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SCREENING;

EID: 0037484660     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000502)39:9<1602::AID-ANIE1602>3.0.CO;2-N     Document Type: Article

References (30)

1. a) K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374-4376;
2. b) R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144.
3. Reviews: a) W. A. Herrmann in Applied Homogeneous Catalysis with Organometallic Compounds (Eds.: B. Cornils, W. A. Herrmann), WILEY-VCH, Weinheim, 1996, pp. 764-765; b) M. Kumada, Pure Appl. Chem. 1980, 52, 669-679.
4. Reviews: a) W. A. Herrmann in Applied Homogeneous Catalysis with Organometallic Compounds (Eds.: B. Cornils, W. A. Herrmann), WILEY-VCH, Weinheim, 1996, pp. 764-765; b) M. Kumada, Pure Appl. Chem. 1980, 52, 669-679.
5. Reviews: a) L. Pu, Chem. Rev. 1998, 98, 2405-2494; b) E.-i. Negishi, F. Liu in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), WILEY-VCH, Weinheim, 1998, pp. 1-48.
6. Reviews: a) L. Pu, Chem. Rev. 1998, 98, 2405-2494; b) E.-i. Negishi, F. Liu in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), WILEY-VCH, Weinheim, 1998, pp. 1-48.
7. Reviews: R. Stürmer, Angew. Chem. 1999, 111, 3509-3510; Angew. Chem. Int. Ed. 1999, 38, 3307-3308.
8. Reviews: R. Stürmer, Angew. Chem. 1999, 111, 3509-3510; Angew. Chem. Int. Ed. 1999, 38, 3307-3308.
9. J. Huang, S. P. Nolan, J. Am. Chem. Soc. 1999, 121, 9889-9892.
10. B. H. Lipshutz, T. Tomiolka, P. A. Blomgren, J. A. Sclafani, Inorg. Chim. Acta 1999, 296, 164-169.
11. Reviews: a) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2476-2514; b) R. H. Crabtree, Chem. Commun. 1999, 1611-1616; c) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889.
12. Reviews: a) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2476-2514; b) R. H. Crabtree, Chem. Commun. 1999, 1611-1616; c) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889.
13. Reviews: a) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2476-2514; b) R. H. Crabtree, Chem. Commun. 1999, 1611-1616; c) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889.
14. Reviews: a) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2476-2514; b) R. H. Crabtree, Chem. Commun. 1999, 1611-1616; c) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889.
15. In total more than 350 metal/ligand combinations were tested.
16. 19F NMR spectroscopy are, for example, high sensitivity, a large resonance area, no need for deuterated solvents, commercial availability of fluorinated substrates, and the inertness of C-F bonds.
17. Reviews: a) J. Burdeniuc, B. Jedlicka, R. H. Crabtree, Chem. Ber. 1997, 130, 145-154; b) J. L. Kiplinger, T. G. Richmond, C. E. Osterberg, Chem. Rev. 1994, 94, 373-431.
18. Reviews: a) J. Burdeniuc, B. Jedlicka, R. H. Crabtree, Chem. Ber. 1997, 130, 145-154; b) J. L. Kiplinger, T. G. Richmond, C. E. Osterberg, Chem. Rev. 1994, 94, 373-431.
19. For details on ligand synth esis, reaction conditions, screening results, ligands employed, and product distributions, see Supporting Information.
20. Review: W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187.
21. Review: W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187.
22. a) A. J. Arduengo III (Du Pont), US-A 5077414, 1991 [Chem. Abstr. 1992, 116, P106289c];
23. a) A. J. Arduengo III (Du Pont), US-A 5077414, 1991 [Chem. Abstr. 1992, 116, P106289c];
24. b) W. A. Herrmann, C. Köcher, L. J. Gooßen, G. R. J. Artus, Chem. Eur. J. 1996, 2, 1627-1636.
25. Review on imidazolium salts as ionic liquids: a) P. Wasserscheid, Angew. Chem. 2000, 112, in press; Angew. Chem. Int. Ed. 2000, 39, in press; b) T. Welton, Chem. Rev. 1999, 99, 2071-2083.
26. Review on imidazolium salts as ionic liquids: a) P. Wasserscheid, Angew. Chem. 2000, 112, in press; Angew. Chem. Int. Ed. 2000, 39, in press; b) T. Welton, Chem. Rev. 1999, 99, 2071-2083.
27. Review on imidazolium salts as ionic liquids: a) P. Wasserscheid, Angew. Chem. 2000, 112, in press; Angew. Chem. Int. Ed. 2000, 39, in press; b) T. Welton, Chem. Rev. 1999, 99, 2071-2083.
28. G. Smith, J. K. Kochi, J. Organomet. Chem. 1980, 198, 199-214.
29. a) P. L. Arnold, F. G. N. Cloke, T. Geldbach, P. B. Hitchcock, Organometallics 1999, 18, 3228-3233;
30. b) A. J. Arduengo III, S. F. Gamper, J. C. Calabrese, F. Davidson, J. Am. Chem. Soc 1994, 116, 4391-4394.