Synthesis and stereochemistry of the first chiral (imidazolinylidence)- and (triazolinylidene)palladium(ii) complex

Chemische Berichte

Volumn 129, Issue 12, 1996, Pages 1483-1488

  Enders, Dieter ^a,b   Gielen, Heike ^a,b   Raabe, Gerhard ^a,b   Runsink, Jan ^a,b   Teles, J Henrique ^a,b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b BASF SE   (Germany)

Author keywords

(carbene)palladium complexes; Axial chirality; Chiral carbenes; Nomenclature

Indexed keywords

EID: 0000868901     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19961291213     Document Type: Article

References (50)

1. H.-W. Wanzlick, Annen: Chem. 1962, 74, 129;
2. Angew. Chem. Int. Ed. Engl. 1962, 1, 75.
3. [2a] A. J. Arduengo III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361.
4. [2b] A. J. Arduengo III: J. G. Goerlich, W. J. Marshall, ibid. 1995, 117, 11027.
5. D. Enders. K. Breuer, G. Raabe. I Runsink. J. H. Teles. J.-P. Melder. K. Ebel, S. Brode, Angew. Chem. 1995. 107, 1119;
6. Augew. Chem. Int. Ed. Engl. 1995, 34, 1021.
7. R. W. Alder. P. R. Allen. M. Murray. A. G. Orpe, Augen: Chem. 1996, 108, 1211;
8. Angew. Chem. Int. Ed. Engl. 1996, 35, l 121.
9. H.-W. Wanzlick, H.-J. Schönherr, Angew. Chem. 1968, 80, 154;
10. Angew. Chem. Int. Ed. Engl. 1968, 7. 141.
11. [6a] K. Öfele, Angew. Chem. 1969, 81, 936;
12. Angew. Chem. Int. Ed. Engl. 1969, 8, 916.
13. [6b] K. Öfele, J. Organomet Chem. 1968, 12, P42.
14. R. J. Sundberg. R. F. Bryan, L F. Taylor. H. Taube, J. Am. Chem. Soc. 1974, 96, 381.
15. For a review, see M. F. Lappert, J. Organomet. Chem. 1988, 358, 185.
16. A. J. Arduengo HI, H. V. R. Dias, J. C. Calabrese, F. Davidson, Organometallics 1993, 12, 3405.
17. A. J. Arduengo III, S. F. Gamper, I C. Calabrese. F. Davidson, J. Am. Chem. Soc. 1994, 116, 4391.
18. [11a] K. Örele, W. A. Hcrrmann, D. Mihauos, VI. Elison. E. Herdtweck, W. Scherer, J. Mink, J. Organomet. Chem. 1993. 459, 177.
19. [11b] K. Öfele, W. A. Herrmann, D. Mihaiios, M. Elison. E. Herdtweck. T. Prierrneicr, P. Kiprof, ibid 1995. 498, 1.
20. N. Kuhn, T. Kratz, R. Boese, D. Bläser, J. Organomet. Chem. 1994, 470, C8.
21. H. Schumann, M. Glanz. J. Winterfeld, H. Hemling, N. Kuhn, T. Kratz, Chem. Ber. 1994, 127. 2369.
22. [14a] W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602;
23. Angew. Chem. Int. Ed. Engl. 1995, 34, 2317.
24. [14b] W. A. Herrmann. M. Eiison. J. Fischer, C. Köcher, G. R. J. Anus, Chem. Ear. J. 1996. 2, 772.
25. For a recent review of carbene chemistry, see M. Regitz, Angew. Chem. 1996, 108, 791;
26. Angew. Chem. Int. Ed. Engl. 1996, 35, 725.
27. [16a] A. W. Coleman, P. B. Hitchcock, M. F. Lappert, R. K. Maskell, J. H. Müller, J. Organomet. Chem. 1983, 250, C9.
28. [16bl A. W. Coleman. P. B. Hitchcock, M. F. Lappert, R. K. Maskell, J. H. Müller, ibid. 1985, 296, 173.
29. E. Keller, Chem. Unterer Zeit 1986, 20, 178.
30. -3 Further details of the crystal structure investigation are available from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the depository number CSD-380117.
31. [19a] G. M. Sheldrick in Crvstallographic Comnutmg 3 (Eds.: G. M. Sheldrick, C. Krüger, R. Goddard), Oxford University Press, 1985, p. 175-189.
32. [19b] Xtal3.2 Reference Manual (Eds.: S. R. Hail, H. D. Flack, J. M. Stewart), Universities of Western Australia, Geneva and Maryland. Lamb, Perth, 1992.
33. K. R. Dixon, A. C. Dixor. in Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson, R. J. Puddephatt). Elsevier, Oxford-New York-Tokyo, 1995. 9, 193.
34. R. E. Cramer, P. L. Dahlstrom, Inorg. Chem. 1985, 24, 3420.
35. R. S. Cahn, C. Ingold, V. Prciog, Angew. Chem. 1966, 78, 413;
36. Angew. Chem. Im. Ed. Engl 1966, J. 385.
37. Preliminary crystallographic investigations show the dinuclear character of these compounds, however, the quality of the crystals does not allow a clean refinement.
38. [24a] J. Chatt. L. M. Venanzi, J. Chem. Soc: 1957, 2.351.
39. [24b] N. W. Alcock, W. L. Wilson. .!. H. Nelson, Inorg. Chem. 1993, 32. 3193.
40. [24c] A. D. Ryabov, L. G. Kuz'mina, V. A. Polyakcv, G. M. Kazankov, E. S. Ryabova, M. Pfeffer. R. van Eldik, J. Chem. Soc. Dalton Trans. 1995, 999.
41. F. Paul, J. Patt, J. F. Hartwig, Orgtmometallics 1995, 14, 3030.
42. For a review of the Heck reaction, see A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473;
43. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
44. [27a] A. J. Catily, Acc. Chem, Res. 1992, 25, 83.
45. [25b] W. A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989;
46. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844.
47. For the preparation and further applications of imidazolium and triazolium salts, see
48. [28a] 1 H. Teles, J.-P. Melder, K. Ebel, R. Schneider, E. Gehrer, W. Harder, S. Brode, D. Enders, K. Breuer, G. Raabe, Helv. Chim. Ada 1996, 79, 61 and references cited therein.
49. [28b] D. Enders, K. Breuer, J. H. Teles, Helv. Chim. Acia 1996, 79, 1217.
50. D. Enders, H. Eichenauer, Cliem. Ber. 1979, 112, 2933.