Ambiphilic compounds: Synthesis and structure of a phosphane-borane with a flexible diphenyl ether tether

European Journal of Organic Chemistry

Volumn , Issue 27, 2007, Pages 4483-4486

  Bebbington, Magnus W P ^a   Bouhadir, Ghenwa ^a   Bourissou, Didier ^a  

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

Author keywords

Ambiphilic derivatives; Boranes; Lithiation; Phosphanes; Solvent effects; Tethered compounds

Indexed keywords

EID: 34748885105     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700538     Document Type: Article

References (51)

1. For example, see: Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, vols. I-III.
2. a) S. Bontemps, H. Gornitzka, G. Bouhadir, K. Miqueu, D. Bourissou, Angew. Chem. Int. Ed. 2006, 45, 1611-1614;
3. Angew. Chem. 2006, 118, 1641-1644;
4. b) S. Bontemps, G. Bouhadir, K. Miqueu, D. Bourissou, J. Am. Chem. Soc. 2006, 128, 12056-12057;
5. c) S. Bontemps, G. Bouhadir, P. W. Dyer, K. Miqueu, D Bourissou, Inorg. Chem. 2007, 46, 5149-5151.
6. a) A related P → Ru-H → B interaction was obtained by borane insertion into a Ru-C bond: R. T. Baker, J. C. Calabrese, S. A. Westcott, T. B. Marder, J. Am. Chem. Soc. 1995, 117, 8777-8784;
7. 2: J. Vergnaud, T. Ayed, K. Hussein, L. Vendier, M. Grellier, G. Bouhadir, J.-C. Barthelat, S. Sabo-Etienne, D. Bourissou, Dalton Trans. 2007, 2370-2372.
8. Transition metal → borane interactions were first structurally authenticated within metallaboratranes: A. F. Hill, G. R. Owen, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. 1999, 38, 2759-2761;
9. Angew. Chem. 1999, 111, 2920-2923.
10. For recent discussions on the precise nature of such interactions, see: a) A. F. Hill, Organometallics 2006, 25, 4741-4743;
11. b) G. Parkin, Organometallics 2006, 25, 4744-4747.
12. For Cp complexes featuring boryl bridges or pendant boryl groups, see: a) W. E. Piers, Chem. Eur. J. 1998, 4, 13-18;
13. b) S. J. Lancaster, S. Al-Benna, M. Thornton-Pett, M. Bochmann, Organometallics 2000, 19, 1599-1608;
14. c) H. Braunschweig, F. M. Breitling, E. Gullo, M. Kraft, J. Organomet. Chem. 2003, 680, 31-42;
15. d) M. Hill, G. Kehr, R. Froḧlich, G. Erker, Eur. J. Inorg. Chem. 2003, 3583-3589;
16. e) S. Aldridge, C. Bresner, Coord. Chem. Rev. 2003, 244, 71-92;
17. f) M. Hill, G. Erker, G. Kehr, R. Fröhlich, O. Kataeva, J. Am. Chem. Soc. 2004, 126, 11046-11057.
18. The activation of a Ni-methyl bond with a phosphanylalane was reported in the context of silane polymerization: F.-G. Fontaine, D. Zargarian, J. Am. Chem. Soc. 2004, 126, 8786-8794.
19. Boron analogues of DIOP were simultaneously and independently investigated by Kagan and Jacobsen: a) A. Börner, J. Ward, K. Kortus, H. B. Kagan, Tetrahedron: Asymmetry 1993, 4, 2219-2228;
20. b) L. B. Fields, E. N. Jacobsen, Tetrahedron: Asymmetry 1993, 4, 2229-2240.
21. a) G. C. Welch, R. R. San Juan, J. D. Masuda, D. W. Stephan, Science 2006, 314, 1124-1126;
22. b) G. J. Kubas, Science 2006, 314, 1096-1097.
23. For examples of PB compounds with unusual optical or ion-sensing properties, see: a) Z. Yuan, N. J. Taylor, Y. Sun, T. B. Marder, I. D. Williams, L.-T. Cheng, J. Organomet. Chem. 1993, 449, 27-37;
24. b) T. Agou. J. Kobayashi, T. Kawashima, Org. Lett. 2005, 7, 4373-4376;
25. c) T. Agou, J. Kobayashi, T. Kawashima, Inorg. Chem. 2006, 45, 9137-9144;
26. d) M. H. Lee, T. Agou, J. Kobayashi, T. Kawashima, F. P. Gabbai, Chem. Commun. 2007, 1133-1135.
27. M. W. P. Bebbington, S. Bontemps, G. Bouhadir, D. Bourissou, Angew. Chem. Int. Ed. 2007, 46, 3333-3336;
28. Angew. Chem. 2007, 119, 3397-3400.
29. H. Braunschweig, R. Dirk, B. Ganter, J. Organomet. Chem. 1997, 545-546, 257-266.
30. For selected examples of DPEphos-type ligands, see: a) M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer, P. W. N. M. van Leeuwen, K. Goubitz, J. Fraanje, Organometallics 1995, 14, 3081-3089;
31. b) M. Caporali, C. Müller, B. B. P. Staal, D. M. Tooke, A. L. Spek, P. W. N. M. van Leeuwen, Chem. Commun. 2005, 3478-3480.
32. For general discussions on the influence of the bite angle of POP ligands, see: c) P. Dierkes, P. W. N. M. van Leeuwen, J. Chem. Soc. Dalton Trans. 1999, 1519-1529;
33. d) Z. Freixa, P. W. N. M. van Leeuwen, Dalton Trans. 2003, 1890-1901.
34. a) D. J. H. Emslie, J. M. Blackwell, J. F. Britten, L. E. Harrington, Organometallics 2006, 25, 2412-2414;
35. b) S. R. Oakley, K. D. Parker, D. J. H. Emslie, I. Vargas-Baca, C. M. Robertson, L. E. Harrington, J. F. Britten, Organometallics 2006, 25, 5835-5838.
36. M. P. Olmsted, P. N. Craig, J. J. Lafferty, A. M. Pavloff, C. L. Zirkle, J. Org. Chem. 1961, 26, 1901-1907.
37. C. J. Dinsmore, C. B. Zartman, Tetrahedron Lett. 1999, 40, 3989-3990.
38. For a relevant example, see: D. Clive, A. G. Angoh, S. M. Bennett, J. Org. Chem. 1987, 52, 1339-1342.
39. L. A. van der Veen, P. H. Keeven, G. C. Schoemaker, J. N. H. Reek, P. C. J. Kamer, P. W. N. van Leeuwen, M. Lutz, A. L. Spek, Organometallics 2000, 19, 872-883.
40. a) O. Desponds, M. Schlosser, J. Organomet. Chem. 1996, 507, 257-261;
41. b) M. Cereghetti, W. Arnold, E. A. Broger, A. Rageot, Tetrahedron Lett. 1996, 37, 5347-5350;
42. c) F. Leroux, H. Mettler, Synlett 2006, 766-770.
43. Coordinating solvents have been shown to accelerate some reactions of organolithiums. For an example in the case of lithium-halogen exchange, see: B. Jedlicka, R. H. Crabtree, P. E. M. Siegbahn, Organometallics 1997, 16, 6021-6023.
44. Free triarylboranes typically display 11B chemical shifts around 70 ppm: a) N. M. D. Brown, F. Davidson, J. W. Wilson, J. Organomet. Chem. 1981, 209, 1-11;
45. b) H. C. Brown, U. S. Racherla, J. Org. Chem. 1986, 51, 427-432.
46. Aryldimesitylboranes do not normally bind fragments larger than fluoride, see: C. D. Entwistle, T. B. Marder, Chem. Mater. 2004, 16, 4574-4585.
47. For a review of directed orrto-metallations in the synthesis of biaryls, see: E. J.-G. Anctil, V. Snieckus, J. Organomet. Chem. 2002, 653, 150-160.
48. A Scifinder Scholar search revealed only symmetrical derivatives of DPEphos.
49. Similar behaviour was reported for the widely used dialkyl biarylphosphanes, see: T. E. Barder, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 5096-5101.
50. G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473.
51. G. M. Sheldrick, SHELXL-97: Program for Crystal Structure Refinement, University of Göttingen, 1997.