The Di-t-butylphosphinyl Directed ortho Metalation Group. Synthesis of hindered dialkylarylphosphines

Synlett

Volumn , Issue 4, 1998, Pages 422-424

  Gray, Matthew ^a,b   Chapell, Brian J ^a   Felding, Jakob ^a,c   Taylor, Nicholas J ^a   Snieckus, Victor ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

^b GLAXOSMITHKLINE   (United Kingdom)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042589976     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1655     Document Type: Article

References (27)

1. Snieckus, V. Chem. Rev. 1990, 90, 879.
2. a) Stuckwisch, C. G. J. Org. Chem. 1976, 41, 1173;
3. b) Dashan, L.; Trippelt, S. Tetrahedron Lett. 1983, 24, 2039;
4. c) Yoshifuji, M.; Ishizuka, T.; Choi, Y. J.; Inamoto, N. Tetrahedron Lett. 1984, 25, 553;
5. d) Schaub, B.; Jenny, T.; Schlosser, M. Tetrahedron Lett. 1984, 25, 4097;
6. e) Craig, D. C.; Roberts, N. K.; Tanswell, J. L. Aust. J. Chem. 1990, 43, 1487.
7. 3PO with t-BuLi leads, in addition to ortho-metalation, to Ph displacement by t-Bu, and further ortho-lithiation: see ref 4d and Seyferth, D.; Welch, D. E.; Heeren, J. K. J. Am. Chem. Soc. 1964, 86, 1100.
8. Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Helv. Chim. Acta 1991, 74, 370.
9. Brown, J. M.; Woodward, S. J. Org. Chem. 1991, 56, 6803;
10. Alcock, N. W.; Brown, J. M.; Pearson, M.; Woodward, S. Tetrahedron Asymmetry 1992, 3, 17.
11. Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27.
12. Togni, A. Chimia 1996, 50, 86.
13. Supported by X-ray crystal structure data (2.498 Å).
14. Complete crystallographic data for compounds 1, 2f, and 11 has been deposited with the Cambridge Crystallographic Data Centre.
15. Mann, B.E.; Shaw, B.L.; Slade, R.M. J. Chem. Soc. (A) 1971, 2976.
16. 2O, no product was isolated.
17. 22IOP: C, 46.17; H, 6.09; P, 8.50. Found: C, 45.95; H, 5.89; P, 8.69.
18. 3, T = 160K. Data were collected on a Siemens P4 Diffractometer with MoKa radiation (λ = 0.71073 Å). A total of 3689 independant reflections were measured. The structure was solved using direct methods (SHELXTL IRIS) and refined by full-matrix least-squares on F (270 parameters) resulting in final R, wR, and GoF values of 4.17, 5.32, and 3.56 respectively [for 2731 data with F > 6.0σ(F)]. The compound co-crystallized with a disordered hexane molecule (compound : solvent = 2:1).
19. Comparison with structures of other phosphine oxides (Haque, M.-u.; Ahmed, J.; Horne, W. Acta Cryst. 1983, C39, 383;
20. Campbell, J.A.; Caughlan, C.N.; Fitzgerald, A.; Campana, C.; Cremer, S.E. Acta Cryst. 1984, C40, 1918) shows a slightly longer than average P-O bond length (1.533 Å).
21. Similar comparison with trigonal planar boronate esters (Matsubara, H.; Tanaka, T.; Takai, Y.; Sawada, M.; Seto, K.; Imazaki, H.; Takahashi, S. Bull. Chem. Soc. Jpn. 1991, 64, 2103;
22. Kliegel, W.; Preu, L.; Rettig, S.J.; Trotter, J. Can. J. Chem. 1986, 64, 1855) and tetrahedral borates
23. 31P NMR chemical shift (79.5 ppm) suggests that the tetrahedral structure dominates in solution as well as in the solid state.
24. 3 / MeCN) in 60% and 63% overall yields respectively. Compounds 7a and 7b were prepared from the corresponding bromo derivatives according to the protocol in Scheme 2 (73 and 58% yields respectively).
25. Iwao, M.; Iihama, T.; Mahalanabis, K.K.; Perrier, H.; Snieckus, V. J. Org. Chem. 1989, 54, 24 (see particularly footnote 9).
26. Sibi, M.P.; Snieckus, V. J. Org. Chem. 1983, 48, 1935.
27. For recent references and extensions, see James, C.A.; Snieckus, V. Tetrahedron Lett. 1997, 38, 8149.