Coordination chemistry of ene-1,1-diamines and a prototype "carbodicarbene"

Angewandte Chemie - International Edition

Volumn 47, Issue 17, 2008, Pages 3210-3214

  Fürstner, Alois ^a   Alcarazo, Manuel ^a   Goddard, Richard ^a   Lehmann, Christian W ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Allenes; Carbenes; Enamines; Gold; Ylides

Indexed keywords

ACIDS; AMINES; CHEMICAL REACTIONS; GOLD COMPOUNDS; LIGANDS; METAL COMPLEXES; METALLIC COMPOUNDS; OLEFINS; TRANSITION METALS;

ALLENES; CARBENES; ENAMINES; GOLD; YLIDES;

COORDINATION REACTIONS;

EID: 47949083075     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705798     Document Type: Article

References (64)

1. General reviews on alkene-1,1-diamines: a) W. Kantlehner in Science of Synthesis Vol. 24 (Ed.: A. de Meijere), Thieme, Stuttgart, 2006, pp. 571-705;
2. b) P. A. Keller, J. Morgan in Science of Synthesis Vol. 24 (Ed.: A. de Meijere), Thieme, Stuttgart, 2006, pp. 707-746.
3. N. Kuhn, A. Abu-Rayyan, A. Al-Sheikh, K. Eichele, C. Maichle- Mößmer, M. Steimann, K. Sweidan, Z. Naturforsch. B 2005, 60, 294-299.
4. a) N. Kuhn, H. Bohnen, J. Kreutzberg, D. Bläser, R. Boese, J. Chem. Soc. Chem. Commun. 1993, 1136-1137;
5. b) N. Kuhn, H. Bohnen, G. Henkel, J. Kreutzberg, Z. Naturforsch. B 1996, 51, 1267-1278.
6. a) P. P. Ponti, J. C. Baldwin, W. C. Kaska, Inorg. Chem. 1979, 18, 873-875;
7. b) N. Kuhn, H. Bohnen, D. Bläser, R. Boese, Chem. Ber. 1994, 127, 1405-1407;
8. c) H. Schuhmann, M. Glanz, J. Winterfeld, H. Hemling, N. Kuhn, H. Bohnen, D. Bläser, R. Boese, J. Organomet. Chem. 1995, 493, C14-C18.
9. A. FArstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519;
10. Angew. Chem. Int. Ed. 2007, 46, 3410-3449.
11. a) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403;
12. b) E. Jiménez-Núñez, A. M. Echavarren, Chem. Commun. 2007, 333-346;
13. c) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105;
14. Angew. Chem. Int. Ed. 2006, 45, 7896-7936.
15. For pioneering studies on other well characterized ketene-N,X-acetals, see a) H. Böhme, F. Soldan, Chem. Ber. 1961, 94, 3109-3119;
16. b) A. I. Meyers, N. Nazarenko, J. Am. Chem. Soc. 1972, 94, 3243-3245;
17. c) H. Quast, L. Bieber, Angew. Chem. 1975, 87, 422-423;
18. Angew. Chem. Int. Ed. Engl. 1975, 14, 428-429;
19. d) C. Reichardt, N. Kaufmann, Chem. Ber. 1985, 118, 3424-3427;
20. e) H. Quast, M. Ach, M. K. Kindermann, P. Rademacher, M. Schindler, Chem. Ber. 1993, 126, 503-516;
21. f) U. Gruseck, M. Heuschmann, Chem. Ber. 1987, 120, 2053-2064.
22. For a compilation of structural data, see E. J. Fernández, A. Laguna, M. E. Olmos, Adv. Organomet. Chem. 2005, 52, 77-141.
23. Anisotropic displacement parameters are drawn at the 50% probability level. Hydrogen atoms have been omitted for clarity, except those residing on the aurated carbon atoms. CCDC 670968 (8), 670969 (14a), 670970 (7), 670971 (12), 670972 (4), 670973 (19), and 671017 (9) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Short crystallographic summaries are found in the Supporting Information.
24. a) A. R. Chianese, X. Li, M. C. Janzen, J. W. Faller, R. H. Crabtree, Organometallics 2003, 22, 1663-1667;
25. b) W. A. Herrmann, J. Schütz, G. D. Frey, E. Herdtweck, Organometallics 2006, 25, 2437-2448.
26. 2L], see: A. Fürstner, M. Alcarazo, H. Krause, C. W. Lehmann, J. Am. Chem. Soc. 2007, 129, 12 676-12677 and its Supporting Information.
27. a) A. J. Arduengo, Acc. Chem. Res. 1999, 32, 913-921;
28. b) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39-91;
29. c) W. A. Herrmann, Angew. Chem. 2002, 114, 1342-1363;
30. Angew. Chem. Int. Ed. 2002, 41, 1290-1309;
31. d) F. E. Hahn, Angew. Chem. 2006, 118, 1374-1378;
32. Angew. Chem. Int. Ed. 2006, 45, 1348-1352;
33. e) N-Heterocyclic Carbenes in Synthesis (Ed.: S. P. Nolan), Wiley-VCH, Weinheim, 2006;
34. f) "N-Heterocyclic Carbenes in Transition Metal Catalysis": Topics in Organometalic Chemistry, Vol. 21 (Ed.: F. Glorius), Springer, Berlin, 2007;
35. g) for an extensive literature overview, also see: D. Kremzow, G. Seidel, C. W. Lehmann, A. Fürstner, Chem. Eur. J. 2005, 11, 1833-1853.
36. [12]
37. S. Marrot, T. Kato, H. Gornitzka, A. Baceiredo, Angew. Chem. 2006, 118, 2660-2663;
38. Angew. Chem. Int. Ed. 2006, 45, 2598-2601.
39. Prepared by the method described in: L. A. M. Bastiaansen, A. A. Macco, E. F. Godefroi, J. Chem. Soc. Chem. Commun. 1974, 36.
40. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 2 1987, S1-S19.
41. Gold enolates: a) Y. Ito, M. Inouye, M. Suginome, M. Murakami, J. Organomet. Chem. 1988, 342, C41-C44;
42. b) M. Murakami, M. Inouye, M. Suginome, Y. Ito, Bull. Chem. Soc. Jpn. 1988, 61, 3649-3652;
43. c) A. N. Nesmeyanov, É. G. Perevalova, V. P. Dyadchenko, K. I. Grandberg, Izv. Akad. Nauk SSSR Ser. Khim 1974, 2872.
44. R. M. Acheson, J. Woollard, J. Chem. Soc. Perkin Trans. 1 1975, 744-748.
45. a) The concept of "slippage" was introduced in: O. Eisenstein, R. Hoffmann, J. Am. Chem. Soc. 1981, 103, 4308-4320;
46. b) for recent Car-Parinello molecular dynamics calculations, see H. M. Senn, P. E. Blöchl, A. Togni, J. Am. Chem. Soc. 2000, 122, 4098-4107;
47. c) for an early structural manifestation of "slippage" in complexes bearing enamine ligands, see T. C. T. Chang, B. M. Foxman, M. Rosenblum, C. Stockman, J. Am. Chem. Soc. 1981, 103, 7361-7362;
48. d) R. McCrindle, G. Ferguson, G. J. Arsenault, A. J. McAlees, D. K. Stephenson, J. Chem. Res. Miniprint 1984, 3301-3344;
49. e) S. L. Doran, D. B. Brown, C. W. Allen, J. Organomet. Chem. 1988, 340, 111-118.
50. H. G. Viehe, Z. Janousek, R. Gompper, D. Lach, Angew. Chem. 1973, 85, 581-582;
51. Angew. Chem. Int. Ed. Engl. 1973, 12, 566-567.
52. R. Tonner, G. Frenking, Angew. Chem. 2007, 119, 8850-8853;
53. Angew. Chem. Int. Ed. 2007, 46, 8695-8698.
54. R. Tonner, F. Öxler, B. Neumüller, W. Petz, G. Frenking, Angew. Chem. 2006, 118, 8206-8211;
55. Angew. Chem. Int. Ed. 2006, 45, 8038-8042.
56. S. Braverman, M. Cherkinsky, M. L. Birsa in Science of Synthesis, Vol. 18 (Ed.: J. G. Knight), Thieme, Stuttgart, 2005, pp. 282-286.
57. For a gem-dimetalated complex of a carbodiphosphorane, see a) J. Vicente, A. R. Singhal, P. Jones, Organometallics 2002, 21, 5887-5900;
58. b) I. Romeo, M. Bardaji, M. C. Gimeno, M. Laguna, Polyhedron 2000, 19, 1837-1841.
59. S. Pascual, M. Asay, O. Illa, T. Kato, G. Bertrand, N. Saffon-Merceron, V. Branchadell, A. Baceiredo, Angew. Chem. 2007, 119, 9236-9238;
60. Angew. Chem. Int. Ed. 2007, 46, 9078-9080.
61. Z. Janousek, H. G. Viehe, Angew. Chem. 1971, 83, 615-616;
62. Angew. Chem. Int. Ed. Engl. 1971, 10, 574-575.
63. For examples, see a) N. Kuhn, H. Bohnen, T. Kratz, G. Henkel, Liebigs Ann. Chem. 1993, 1149-1151;
64. b) N. Kuhn, M. Göhner, M. Steimann, Z. Anorg. Allg. Chem. 2002, 628, 896-900.