Stille cross-coupling of a racemic planar-chiral ferrocene and crystallographic trace analysis of catalysis intermediates and by-products

Helvetica Chimica Acta

Volumn 90, Issue 4, 2007, Pages 834-845

  Weber, Immo ^a,b   Heinemann, Frank W ^a   Bakatselos, Panagiotis ^a   Zenneck, Ulrich ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b Abteilung Forschung und Entwicklung   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYZED STILLE COUPLING; CRYSTALLOGRAPHIC TRACE ANALYSIS; FERROCENE; X RAY CRYSTAL STRUCTURE;

CATALYSIS; CHIRALITY; CRYSTALLIZATION; CRYSTALLOGRAPHY; SINGLE CRYSTALS; TRACE ANALYSIS;

OLEFINS;

FERROCENE; RAC 1 (PHTHALIMIDOMETHYL) 2 (TRIBUTYLSTANNYL)FERROCENE; RAC 1 [(DIMETHYLAMINO)METHYL] 2 (TRIBUTYLSTANNYL)FERROCENE; RAC 1 PHENYL 2 (N PHTHALIMIDOMETHYL) FERROCENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHROMATOGRAPHY; CRYSTAL STRUCTURE; CRYSTALLIZATION; MASS SPECTROMETRY; MICROSCOPE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STILLE REACTION; X RAY CRYSTALLOGRAPHY;

EID: 34250710173     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200790083     Document Type: Article

References (43)

1. a) 'Ferrocenes', Eds. A. Togni and T. Hayashi, VCH, Weinheim, 1995;
2. b) 'Metallocenes', Eds. A. Togni and L. Hintermann, Wiley-VCH, Weinheim, 1998;
3. c) A. Togni, Angew. Chem. 1996, 108, 1581;
4. d) H.-U. Blaser, W. Brieden, B. Pugin, F. Spindler, M. Studer, A. Togni, Top. Catal. 2002, 19, 3;
5. e) A. Schnyder, L. Hintermann, A. Togni, Angew. Chem., Int. Ed. 1995, 34, 931;
6. f) U. Burckhardt, L. Hintermann, A. Schnyder, A. Togni, Organometallics 1995, 14, 5415;
7. g) R. Dorta, D. Broggini, R. Stoop, H. Rüegger, F. Spindler, A. Togni, Chem. - Eur. J. 2004, 10, 267;
8. h) R. Dorta, D. Broggini, R. Kissner, A. Togni. Chem. - Eur. J. 2004, 10, 4546,
9. i) G. W. Gokel, I. K. Ugi, J. Chem. Educ. 1972, 49, 294.
10. a) L. F. Tietze, H. Ila, H. P. Bell, Chem. Rev. 2004, 104, 3453;
11. b) H. L. Pedersen, M. Johannsen, Chem. Commun. 1999, 2517;
12. c) H. L. Pedersen, M. Johannsen, J. Org. Chem. 2002, 67, 7982;
13. d) E.-i. Negishi, F.-T. Luo, R. Frisbee, H. Matsushita, Heterocycles 1982, 18, 117;
14. e) O. Riant, G. Argouarch, D. Guillaneux, O. Samuel, H. B. Kagan, J. Org. Chem. 1998, 63, 3511.
15. a) J. K. Stille, Angew. Chem., Int. Ed. Engl. 1986, 25, 508 and ref. cit. therein;
16. b) D. Guillaneux, H. B. Kagan, J. Org. Chem. 1995, 60, 2502;
17. c) C.-M. Liu, Y.-L. Guo, Q.-H. Xu, Y.-M. Liamg, Y.-X. Ma, Synth. Commun. 2000, 30, 4405.
18. I. Weber, F. W. Heinemann, W. Bauer, S. Superci, A. Zahl, J. Procelewska, S. Procelewski, D. Richter, U. Zenneck, in preparation; P. Pinto, A. W. Götz, B. A. Hess, A. Marinetti, F. W. Heinemann, G. Marconi, U. Zenneck, Organometallics 2006, 25, 2607;
19. P. Pinto, G. Marconi, F. W. Heinemann, U. Zenneck, Organometallics 2004, 23, 374;
20. G. Marconi, H. Baier, F. W. Heinemann, P. Pinto, H. Pritzkow, U. Zenneck, Inorg. Chim. Acta 2003, 352, 188.
21. a) L. Xiao, K. Mereiter, W. Weissensteiner, M. Widhalm, Synthesis 1999, 8, 1354;
22. b) R. Kitzler, L. Xiao, W. Weissensteiner, Tetrahedron: Asymmetry 2000, 11, 3459;
23. c) U. Behrens, J. Organomet. Chem. 1979, 182, 89.
24. a) O. J. Curnow, G. M. Fern, D. Wöll, Inorg. Chem. Commun. 2003, 6, 1201;
25. b) J. P. Flemming, M. C. Pilon, O. Y. Borbulevitch, M. Y. Antipin, V. V. Grushin, Inorg. Chim. Acta 1998, 280, 87;
26. c) P. E. Fanta, Synthesis 1974, 9;
27. d) G. Bringmann, R. Walter, R. Weirich, Angew. Chem., Int. Ed. 1990, 29, 977;
28. e) A. Patti, D. Lambusta, M. Piattelli, G. Nicolosi, Tetrahedron: Asymmetry 1998, 9, 3037;
29. f) H. Plenio, J. Hermann, A. Sehring, Chem. - Eur. J. 2000, 6, 1820.
30. A. J. Birch, J. Chem. Soc. 1944, 430;
31. A. J. Birch, Pure Appl. Chem. 1996, 68, 553.
32. R. Zelonka, M. Baird, J. Organomet. Chem. 1972, 35, C34;
33. R. Zelonka, M. Baird, Can. J. Chem. 1972, 50, 3036;
34. Y. Miyaki, T. Onishi, H. Kurosawa, Inorg. Chim. Acta 2000, 300-302, 369;
35. G. Marconi, Ph. D. Thesis, Friedrich-Alexander-Universität Erlangen-Nürnberg, 2003;
36. G. Bodes, F. W. Heinemann, G. Marconi, S. Neumann, U. Zenneck, J. Organomet. Chem. 2002, 641, 90;
37. I. Weber, Ph. D. Thesis, Friedrich-Alexander-Universität Erlangen-Nürnberg, 2006.
38. a) Bruker-Nonius, COLLECT, Program for Data Collection, 2002;
39. b) Bruker-Nonius, EvalCCD, Program for Data Reduction, 2002;
40. c) Bruker AXS, SADABS, Program for Absorption Correction, 2002;
41. d) Bruker AXS, SHELXTL NT 6.12, Program for Structure Determination, 2002;
42. e) Bruker AXS, SHELXTL NT 6.12, Program for Structure Refinement, 2002;
43. f) Bruker AXS, SHELXTL NT 6.12, Program for Molecule Projection, 2002.