Taming a functional group: Creating air-stable, chiral primary phosphanes

Angewandte Chemie - International Edition

Volumn 45, Issue 43, 2006, Pages 7248-7251

  Hiney, Rachel M ^a   Higham, Lee J ^a,b   Müller Bunz, Helge ^a   Gilheany, Declan G ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Air stability; Asymmetric catalysis; Conjugation; Electrochemistry; Phosphanes

Indexed keywords

MOLECULAR STRUCTURE; OXIDATION; STABILITY;

AIR STABILITY; ASYMMETRIC CATALYSIS; CONJUGATION; PHOSPHANES;

PHOSPHORUS COMPOUNDS;

PHOSPHINE DERIVATIVE;

AIR; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AIR; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOSPHINES; STEREOISOMERISM;

EID: 33751012734     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602143     Document Type: Article

References (49)

1. a) L. Maier in Organic Phosphorus Compounds, Vol. 1 (Eds.: G. M. Kosolapoff, L. Maier), Wiley-Interscience, New York, 1972, chap. 1, pp. 4-16;
2. b) For example, Rhodia created a safety video for internal use showing spontaneous combustion of primary phosphanes in air to illustrate their pyrophoricity;
3. c) K. V. Katti, N. Pillarsetty, K. Raghuraman, Top. Curr. Chem. 2003, 229, 121-141.
4. a) T. P. Clarke, C. R. Landis, Tetrahedron: Asymmetry 2004, 15, 2123-2137;
5. b) G. Hoge, B. Samas, Tetrahedron: Asymmetry 2004, 15, 2155-2157;
6. c) D. J. Brauer, K. W. Kottsieper, S. Roßenbach, O. Stelzer, Eur. J. Inorg. Chem. 2003, 1748-1755;
7. d) A. Herrbach, A. Marinetti, O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem. 2003, 68, 4897-4905, and references therein;
8. e) S. Chatterjee, M. D. George, G. Salem, A. C. Willis, J. Chem. Soc. Dalton Trans. 2001, 1890-1896.
9. K. V. Katti, H. Gali, C. J. Smith, D. E. Berning, Acc. Chem. Res. 1999, 32, 9-17.
10. H. Dorn, R. A. Singh, J. A. Massey, A. J. Lough, I. Manners, Angew. Chem. 1999, 111, 3540-3543;
11. Angew. Chem. Int. Ed. 1999, 38, 3321-3323.
12. T. Hanaya, H. Yamamoto, Bull. Chem. Soc. Jpn. 1989, 62, 2320-2327.
13. E. P. Kyba, S.-T. Liu, Inorg. Chem. 1985, 24, 1613-1616.
14. M. Brynda, Coord. Chem. Rev. 2005, 249, 2013-2034.
15. a) M. Yoshifuji, K. Shibayama, N. Inamoto, T. Matsushita, K. Nishimoto, J. Am. Chem. Soc. 1983, 105, 2495-2497;
16. b) M. Yoshifuji, K. Shibayama, K. Toyota, N. Inamoto, Tetrahedron Lett. 1983, 24, 4227-4228.
17. G. Ramakrishnan, A. Jouaiti, M. Geoffroy, G. Bernardinelli, J. Phys. Chem. 1996, 100, 10861-10868.
18. a) W. Henderson, S. R. Alley, J. Organomet. Chem. 2002, 656, 120-128.
19. b) N. J. Goodwin, W. Henderson, B. K. Nicholson, J. Fawcett, D. R. Russell, J. Chem. Soc. Dalton Trans. 1999, 1785-1793.
20. D. J. Brauer, J. Fischer, S. Kucken, K. P. Langhans, O. Stelzer, N. Weferling, Z. Naturforsch. B 1994, 49, 1511-1524.
21. a) N. Pillarsetty, K. Raghuraman, C. L. Barnes, K. V. Katti, J. Am. Chem. Soc. 2005, 127, 331-336;
22. b) H. Gali, S. R. Karra, V. S. Reddy, K. V. Katti, Angew. Chem. 1999, 111, 2152-2155;
23. Angew. Chem. Int. Ed. 1999, 38, 2020-2023.
24. L. J. Higham, E. F. Clarke, H. Müller-Bunz, D. G. Gilheany, J. Organomet. Chem. 2005, 690, 211-219.
25. a) R. Schmid, E. A. Broger, M. Cereghetti, Y. Crameri, J. Foricher, M. Lalonde, R. K. Müller, M. Scalone, G. Schoettel, U. Zutter, Pure Appl. Chem. 1996, 68, 131-138;
26. b) L. Dahlenburg, A. Kaunert, Eur. J. Inorg. Chem. 1998, 885-887.
27. -3; CCDC-281451 contains 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.
28. R. A. Bartlett, M. M. Olmstead, P. P. Power, G. A. Sigel, Inorg. Chem. 1987, 26, 1941-1946.
29. Several references with no comment on air stability but giving crystal structure data are given in the Supporting Information.
30. We note 2′-diphenylphosphanyl-1,1′-binaphthyl (Y. Uozumi, N. Suzuki, A. Ogiwara, T. Hayashi, Tetrahedron 1994, 50, 4293-4302)
31. is highly effective in asymmetric hydrosilylation (K. Kitayama, Y. Uozumi, T. Hayashi, J. Chem. Soc. Chem. Commun. 1995, 1533-1534)
32. and cross-coupling reactions (Y. H. Cho, A. Kina, T. Shimada, T. Hayashi, J. Org. Chem. 2004, 69, 3811-3823).
33. [8b] Compounds 4 and 5 are not oxidized over the same time frame but behave similarly if left for very much longer or subjected to more harsh conditions.
34. a) K. B. Oldham, J. Electroanal Chem. 1985, 184, 257-267;
35. b) P. D. Lyne, R. D. O'Neill, Anal. Chem. 1990, 62, 2347-2351.
36. Although these measurements are indicative of a one-electron process at an electrode and not necessarily applicable to oxidation by an oxygen molecule, they do however indicate the relative HOMO energies of the different primary phosphanes.
37. a) H. R. Hudson in The Chemistry of Organophosphorus Compounds, Vol. 1 (Ed.: F. R. Hartley), Wiley, New York, 1990, pp. 438-439, and references therein;
38. b) P. D. Bartlett, E. F. Cox, R. E. Davis, J. Am. Chem. Soc. 1961, 83, 103-109.
39. It should be noted that 1a and 5 were easily oxidized by peroxides in reaction grade THF, but this is an oxidation that takes place by a different mechanistic process; see reference [22a]. H. R. Hudson in The Chemistry of Organophosphorus Compounds, Vol. 1, 1990, pp. 438-439
40. 2 no oxidation of 5 was observed after 25 days.
41. a) D. E. Cabelli, A. H. Cowley, M. J. S. Dewar, J. Am. Chem. Soc. 1981, 103, 3286-3289;
42. b) L. Nyulaszi, D. Szieberth, G. I. Csonka, J. Reffy, J. Heinicke, T. Veszpremi, Struct. Chem. 1995, 6, 1-7;
43. c) K. Miqueu, J-M. Sotiropoulos, G. Pfister-Guillouzo, V. Rudzevich, V. Romanenko, G. Bertrand, Eur. J. Inorg. Chem. 2004, 381-387;
44. d) T. P. Debies, J. W. Rabalais, Inorg. Chem. 1974, 13, 308-312;
45. e) D. G. Gilheany in The Chemistry of Organophosphorus Compounds, Vol. 1 (Ed.: F. R. Hartley), Wiley, 1990, chap. 1, pp. 9-49.
46. We stress that oxidation of neat and dissolved primary phosphanes by air, oxygen, and peroxide are not trivial experiments and stringent safety precautions against fire must be adopted.
47. a) G. M. Sheldrick, SADABS, Bruker AXS Inc., Madison, WI 53711, USA, 2000;
48. b) G. M. Sheldrick, SHELXS-97, University of Gottingen, 1997;
49. c) G. M. Sheldrick SHELXL-97-2, University of Gottingen, 1997.