Synthesis and ligand properties of a stable five-membered-ring vinylidenephosphorane

Angewandte Chemie - International Edition

Volumn 47, Issue 39, 2008, Pages 7530-7533

  Asay, Matthew ^a   Kato, Tsuyoshi ^a   Saffon Merceron, Nathalie ^a   Cossío, Fernando P ^c   Baceiredo, Antoine ^a   Bertrand, Guy ^b  

^a UMR 5069) 118 route de Narbonne   (France)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Allenes; Carbenes; Ligands; Phosphorus; Ylides

Indexed keywords

EID: 54749098732     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802741     Document Type: Article

References (64)

1. For recent reviews on stable carbenes, see for examples: a) F. E. Hahn, M. C. Jahnke, Angew. Chem. 2008, 120, 3166-3216;
2. Angew. Chem. Int. Ed. 2008, 47, 3122-3172;
3. b) E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824-2870;
4. Angew. Chem. Int. Ed. 2007, 46, 2768-2813;
5. c) "N-Heterocyclic Carbenes in Transition Metal Catalysis": F. Glorius, Topics in Organometallic Chemistry, Springer, Heidelberg, 2006;
6. d) S. P. Nolan, N-Heterocyclic Carbenes in Synthesis, Wiley-VCH, 2006;
7. e) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39-91.
8. For reviews on ylides and carbodiphosphoranes, see: a) O. I. Kolodiazhnyi, Tetrahedron 1996, 52, 1855-1929;
9. b) O. I. Kolodiazhnyi, Phosphorus Ylides: Chemistry and Application in Organic Synthesis, Wiley-VCH, Weinheim, 1999;
10. c) H. M. Cristau, Chem. Rev. 1994, 94, 1299-1313.
11. S. Marrot, T. Kato, H. Gornitzka, A. Baceiredo, Angew. Chem. 2006, 118, 2660-2663;
12. Angew. Chem. Int. Ed. 2006, 45, 2598-2601.
13. a) Y. Canac, M. Soleilhavoup, S. Conejero, G. Bertrand, J. Organomet. Chem. 2004, 689, 3857-3865;
14. b) V. Lavallo, Y. Canac, C. Präsang, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 5851-5855;
15. Angew. Chem. Int. Ed. 2005, 44, 5705-5709;
16. c) V. Lavallo, Y. Canac, A. DeHope, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 7402-7405;
17. Angew. Chem. Int. Ed. 2005, 44, 7236-7239;
18. d) V. Lavallo, J. Mafhouz, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, J. Am. Chem. Soc. 2004, 126, 8670-8671.
19. For discussions on the electronic structure of carbodiphosphoranes, see: a) R. Tonner, F. Öxler, B. Neumüller, W. Petz, G. Frenking, Angew. Chem. 2006, 118, 8206-8211;
20. Angew. Chem. Int. Ed. 2006, 45, 8038-8042;
21. b) H. Schmidbaur, Angew. Chem. 2007, 119, 3042-3043;
22. Angew. Chem. Int. Ed. 2007, 46, 2984-2985;
23. c) G. Frenking, B. Neumüller, W. Petz, R. Tonner, F. Öxler, Angew. Chem. 2007, 119, 3044-3045;
24. Angew. Chem. Int. Ed. 2007, 46, 2986-2987.
25. a) C . A. Dyker, V. Lavallo, B. Donnadieu, G. Bertrand, Angew. Chem. 2008, 120, 3250-3253;
26. Angew. Chem. Int. Ed. 2008, 47, 3206-3209;
27. b) V. Lavallo, C. A. Dyker, B. Donnadieu, G. Bertrand, Angew. Chem. 2008, DOI: 10.1002/ange.200801176;
28. Angew. Chem. Int. Ed. 2008, DOI: 10.1002/anie.200801176.
29. For calculations on carbodicarbenes, see: a) R. Tonner, G. Frenking, Angew. Chem. 2007, 119, 8850-8853;
30. Angew. Chem. Int. Ed. 2007, 46, 8695-8698;
31. b) R. Tonner, G. Frenking, Chem. Eur. J. 2008, 14, 3260-3272;
32. c) R. Tonner, G. Frenking, Chem. Eur. J. 2008, 14, 3273-3289.
33. For other papers related to bent allenes, see: a) O. Kaufhold, F. E. Hahn, Angew. Chem. 2008, 120, 4122-4126;
34. Angew. Chem. Int. Ed. 2008, 47, 4057-4061;
35. b) A. Fürstner, M. Alcarazo, R. Goddard, C. W. Lehmann, Angew. Chem. 2008, 120, 3254-3258;
36. Angew. Chem. Int. Ed. 2008, 47, 3210-3214.
37. a) R. W. Saalfrank, H. Maid, Chem. Commun. 2005, 5953-5967;
38. b) R. W. Saalfrank, W. Paul, H. Libenow, Angew. Chem. 1980, 92, 740-741;
39. Angew. Chem. Int. Ed. Engl. 1980, 19, 713-714;
40. c) R. W. Saalfrank, Isr. J. Chem. 1985, 26, 181-190.
41. M. Soleilhavoup, A. Baceiredo, O. Treutler, R. Ahlrichs, M. Nieger, G. Bertrand, J. Am. Chem. Soc. 1992, 114, 10959-10961.
42. H. J. Bestmann, K. Roth, R. W. Saalfrank, Angew. Chem. 1977, 89, 915-916;
43. Angew. Chem. Int. Ed. Engl. 1977, 16, 877-878.
44. a) D. Birney, T. K. Lim, J. H. P. Koh, B. R. Pool, J. M. White, J. Am. Chem. Soc. 2002, 124, 5091-5099;
45. b) M. Avenati, O. Pilet, P. A. Carrupt, P. Vogel, Helv. Chim. Acta 1982, 65, 178-187.
46. a) A. H. Cowley, R. A. Kemp, J. G. Lasch, N. C. Norman, C. A. Stewart, J. Am. Chem. Soc. 1983, 105, 7444-7445;
47. b) A. H. Cowley, R. A. Kemp, J. G. Lasch, N. C. Norman, C. A. Stewart, B. R. Whittlesey, T. C. Wright, Inorg. Chem. 1986, 25, 740-749.
48. H.-J. Cristau, J. Grenier, P. Lexouret, E. Torreilles, Heteroat. Chem. 1996, 7, 471-480.
49. Phosphines are known to react with carbon tetrachloride: a) R. Appel, H. F. Schoeler, Chem. Ber. 1979, 112, 1068-1070;
50. b) H. Grützmacher, H. Pritzkow, Angew. Chem. 1991, 103, 721-723;
51. Angew. Chem. Int. Ed. Engl. 1991, 30, 709-710;
52. c) U. Heim, H. Pritzkow, H. Schoenberg, H. Grützmacher, J. Chem. Soc. Chem. Commun. 1993, 673-674.
53. CCDC-690713 (4), 690714 (5), and 690715 (6) 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.
54. a) J. C. J. Bart, J. Chem. Soc. B 1969, 350-365;
55. b) H. Burzlaff, U. Voll, H. J. Bestmann, Chem. Ber. 1974, 107, 1949-1956.
56. a) W. Kohn, A. D. Becke, R. G. Parr, J. Phys. Chem. 1996, 100, 12974-12980;
57. b) A. D. Becke, J. Phys. Chem. 1993, 98, 5648-5652;
58. c) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100.
59. For details concerning the calculations, see the Supporting Information.
60. D. G. Gilheany, Chem. Rev. 1994, 94, 1339-1374.
61. K. B. Wiberg, Tetrahedron 1968, 24, 1083-1096.
62. G. D. Frey, V. Lavallo, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2007, 316, 439-441.
63. a) A. Fürstner, M. Alcarazo, H. Krause, C. W. Lehmann, J. Am. Chem. Soc. 2007, 129, 12676-12677;
64. b) A. R. Chianese, X. W. Li, M. C. Janzen, J. W. Faller, R. H. Crabtree, Organometallics 2003, 22, 1663-1667.