Synthesis and characterization of phospha-palladacycles and their catalytic properties in the olefination of chloro- and bromoarenes

Journal of Organometallic Chemistry

Volumn 690, Issue 13, 2005, Pages 3193-3201

  Frey, Guido D ^a   Reisinger, Claus Peter ^b   Herdtweck, Eberhardt ^a   Herrmann, Wolfgang A ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b EXATEC GmbH and Co KG   (Germany)

Author keywords

Catalysis; CC coupling; Chloroarenes; Heck reaction; Palladacycles; Palladium

Indexed keywords

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; CHLORINE COMPOUNDS; NUCLEAR MAGNETIC RESONANCE; OLEFINS; ORGANOMETALLICS; PALLADIUM COMPOUNDS; STYRENE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CC-COUPLING; CHLOROARENES; HECK REACTION; PALLADACYCLES;

CATALYSTS;

EID: 20144370040     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.03.052     Document Type: Article

References (42)

1. T. Mizoroki, K. Mori, and A. Ozaki Bull. Chem. Soc. Jpn. 44 1971 581
2. R.F. Heck, and J.P. Nolly J. Org. Chem. 37 1972 2320
3. R.F. Heck B.M. Trost I. Fleming Comprehensive organic synthesis vol. 4 1991 Pergamon Oxford 833
4. A. de Meijere, and F.E. Meyer Angew. Chem. 106 1994 2473
5. Angew. Chem. Int. Ed. Engl. 33 1994 2379
6. W.A. Herrmann B. Cornils W.A. Herrmann Applied homogeneous catalysis with organometallic compounds vol. 2 2002 VCH 775 Weinheim vol. 3, 2002, p. 1343
7. W.A. Herrmann, C.-P. Reisinger, and P. Härter Aqueous-phase organometallic catalysis second ed. 2004 511
8. W.A. Herrmann, in: W.A. Herrmann, G. Brauer (Eds.), Herrmann/Brauer, Synthetic Methods of Organometallic and Inorganic Chemistry, Thieme, Stuttgart, 2002
9. W.A. Herrmann Angew. Chem. 114 2002 1342
10. Angew. Chem. Int. Ed. Engl. 41 2002 1290
11. A.J. Cheney, and B.L. Shaw J. Chem. Soc., Dalton Trans. 1972 754
12. B.L. Shaw New J. Chem. 1998 77
13. E.C. Aleya, S.A. Dias, G. Ferguson, and P.J. Roberts J. Chem. Soc., Dalton Trans. 1979 948
14. E.C. Aleya, G. Ferguson, J. Malito, and B.L. Ruhl Organometallics 8 1989 1188
15. T. Mitsudo, W. Fischetti, and R.F. Heck J. Org. Chem. 49 1984 1640
16. W.A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, and H. Fischer Angew. Chem. 107 1995 1989
17. Angew. Chem. Int. Ed. Engl. 34 1995 1844
18. W.A. Herrmann, C. Broßmer, C.-P. Reisinger, T.H. Riermeier, K. Öfele, and M. Beller Chem. Eur. J. 3 1997 1357
19. W.A. Herrmann, and V.P.W. Böhm J. Organomet. Chem. 572 1999 141
20. V.P.W. Böhm, and W.A. Herrmann Chem. Eur. J. 6 2000 1017
21. M. Beller, H. Fischer, W.A. Herrmann, K. Öfele, and C. Broßmer Angew. Chem. 107 1995 1992
22. Angew. Chem. Int. Ed. Engl. 34 1995 1848
23. W.A. Herrmann, C.-P. Reisinger, K. Öfele, C. Broßmer, M. Beller, and H. Fischer J. Mol. Catal. A 108 1996 51
24. M. Beller, T.H. Riermeier, C.-P. Reisinger, and W.A. Herrmann Tetrahedron Lett. 38 1997 2073
25. W.A. Herrmann, V.P.W. Böhm, and C.-P. Reisinger J. Chem. Educ. 77 2000 92
26. V.P.W. Böhm, and W.A. Herrmann Chem. Eur. J. 7 2001 4191
27. W.A. Herrmann, K. Öfele, D. v. Preysing, and S.K. Schneider J. Organomet. Chem. 687 2003 229
28. B.L. Shaw, S.D. Perera, and E.A. Staley Chem. Commun. 1998 1361
29. C.-P. Reisinger, Ph.D. Thesis, Technische Universität München, 1997, ISBN 3-933083-00-1
30. W.A. Herrmann, V.P.W. Böhm, and C.-P. Reisinger J. Organomet. Chem. 576 1999 23
31. J. Tsuji Palladium reagents and catalysts 1995 Wiley & Sons Chichester
32. L. Brandsma, S.F. Vasilevsky, and H.D. Verkruijsse Application of transition metal catalysts in organic synthesis 1998 Springer Berlin
33. F. Diederich P.J. Stang Metal-catalyzed cross-coupling reactions 1998 Wiley-VCH Weinheim
34. A.W. Hofmann Justus Liebigs Ann. Chem. 78 1851 553
35. Data Collection Software for Nonius κ-CCD devices, Delft, The Netherlands, 2001
36. Z. Otwinowski, and W. Minor Methods Enzymol. 276 1997 307ff
37. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori, and M. Camalli sir92 J. Appl. Crystallogr. 27 1994 435 436
38. A.J.C. Wilson International tables for crystallography vol. C 1992 Kluwer Academic Publishers Dordrecht, The Netherlands (Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2)
39. A.L. Spek platon, A multipurpose crystallographic tool 2001 Utrecht University Utrecht, The Netherlands
40. G.M. Sheldrick shelxl-97 1998 Universität Göttingen Göttingen (Germany)
41. G.D. Frey, Ph.D. Thesis, Technische Universität München, 2005
42. H. Riihimäki, P. Suomalainen, H.K. Reinius, J. Suutari, S. Jääskeläinen, A.O.I. Krause, T.A. Pakkanen, and J.T. Pursiainen J. Mol. Catal. A: Chem. 200 2003 69