An expedient synthesis of dialkylphosphane-borane complexes from sodium phosphide, and their alkylation under phase-transfer conditions

Synthesis

Volumn , Issue 19, 2007, Pages 2987-2994

  Kasák, Peter ^a   Widhalm, Michael ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

Boron complexes; Phase transfer catalysis; Phosphanes; Phosphorus complexes; Red phosphorus

Indexed keywords

BORON COMPLEXES; PHASE-TRANSFER CATALYSIS; PHOSPHANES; PHOSPHORUS COMPLEXES; RED PHOSPHORUS;

ALKYLATION; COMPLEXATION; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

1,2 BIS{[ 2,5 DIMETHYLPHOSPHOLANYL]METHYL}BENZENE BIS(BORANE); 1,3 BIS 2,5 DIMETHYLPHOSPHOLAN 1 YL]PROPANE BIS(BORANE); 1,3 BIS(DICYCLOPENTYLPHOSPHANYL)PROPANE BIS(BORANE); 1,3 BIS[(DICYCLOPENTYLPHOSPHANYL)METHYL]BENZENE BIS(BORANE); 1,3 BIS{ BIS[2 (BENZYLOXY) 1 METHYLETHYL]PHOSPHANYL}PROPANE BIS(BORANE); 1,3 BIS{[ 2,5 DIMETHYLPHOSPHOLAN 1 YL]METHYL}BENZENE BIS(BORANE); 2,5 DIISOPROPYLPHOSPHOLANE BORANE; 2,5 DIMETHYLPHOSPHOLANE BORANE; 3,5 DIMETHYL 1,4 OXAPHOSPHINANE BORANE; ALLYLDICYCLOPENTYLPHOSPHANE BORANE; BENZYLDICYCLOPENTYLPHOSPHANE BORANE; BIS[2 (1 ETHOXYETHOXY) 2 PHENYLETHYL]PHOSPHANE BORANE; BIS[2 (1 ETHOXYETHOXY)PROPYL]PHOSPHANE BORANE; BIS[2 (BENZYLOXY) 1 METHYLETHYL]PHOSPHANE BORANE; BORANE DERIVATIVE; DIALKYLPHOSPHANE; DICYCLOPENTYLPHOSPHANE BORANE; N,N DIMETHYLFORMAMIDE; PHOSPHINE DERIVATIVE; SODIUM DIHYDROGEN PHOSPHATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; GRIGNARD REACTION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; SYNTHESIS;

EID: 35348988771     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990777     Document Type: Article

References (36)

1. New address: P. Kasák, Polymer Institute of the Slovak Academy of Sciences, Dúbravská cesta 9, 84236 Bratislava, Slovakia.
2. (a) Sasse, K. In Houben-Weyl, Vol. 12/1; Müller, E., Ed.; Thieme: Stuttgart, 1963, 17-65.
3. (b) Eisner, G. In Houben-Weyl, E1; Regitz, M., Ed.; Thieme: Stuttgart, 1982, 132-172.
4. (c) The Chemistry of Organophosphorus Compounds, Vol. 1; Hartley, F. R., Ed.; Wiley: New York, 1990, 152-182.
5. (d) Allen, D. W. In Organophosphorus Chemistry, Vol. 34; Allen, D. W.; Tebby, J. C., Eds.; Royal Society of Chemistry: Cambridge UK, 2005, 1.
6. For biaryl-type bisphosphane ligands, see: (e) Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405.
7. For P-chiral phosphanes, see: (f) Crepy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1.
8. For the preparation of sodium phosphide from red phosphorus and its use in the synthesis of mono- and dialkylphosphanes from alkyl halides, see: (a) Van Hooijdonk, M. C. J. M.; Gerritsen, G.; Brandsma, L. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 162, 39.
9. (b) Brandsma, L.; Gusarova, N. K.; Gusarov, A. V.; Verkruijsse, H. D.; Trofimov, B. A. Synth. Commun. 1994, 24, 3219.
10. (a) Bitterer, F.; Herd, O.; Kühnel, M.; Stelzer, O.; Weferling, N.; Sheldrick, W. S.; Hahn, J.; Nagel, S.; Rösch, N. Inorg. Chem. 1998, 37, 6408.
11. (b) Braun, W.; Calmuschi, B.; Haberland, J.; Hummel, W.; Liese, A.; Nickel, T.; Stelzer, O.; Salzer, A. Eur. J. Inorg. Chem. 2004, 2235.
12. Carboni, B.; Monnier, L. Tetrahedron 1991, 55, 1197.
13. Baudler, M.; Zarkadas, A. Chem. Ber. 1972, 105, 3844.
14. Vasse, J.-L.; Stranne, R.; Zalubovskis, R.; Gayet, C.; Moberg, C. J. Org. Chem. 2003, 68, 3258.
15. Rauhut, M. M.; Currier, H. A.; Semsel, A. M.; Wystrach, V. P. J. Org. Chem. 1961, 26, 5138.
16. (a) Busacca, C. A.; Lorenz, J. C.; Grinberg, N.; Haddad, N.; Hrapchak, M.; Latli, B.; Lee, H.; Sabila, P.; Saha, A.; Sarvestani, M.; Shen, S.; Varsolona, R.; Wei, X.; Senanayake, C. H. Org. Lett. 2005, 7, 4277.
17. (b) Galland, A.; Dobrota, C.; Toffano, M.; Fiaud, J.-C. Tetrahedron: Asymmetry 2006, 17, 2354.
18. (c) Strecker, R. A.; Snead, J. L.; Sollott, G. P. J. Am. Chem. Soc. 1973, 95, 210.
19. Maercker, A.; Geuss, R. Angew. Chem., Int. Ed. Engl. 1970, 9, 909.
20. Grim, S. O.; Molena, R. P. Phosphorus Relat. Group V Elem. 1974, 4, 189.
21. Ostermeier, M.; Prieß, J.; Helmchen, G. Angew. Chem. Int. Ed. 2002, 41, 612.
22. Burk, M. J.; Pizzano, A.; Martin, J. A. Organometallics 2000, 19, 250.
23. 3-symmetric trihydroxy trialkyl phosphane-borane complexes has been submitted recently: Kasák P.; Arion V.; Widhalm M. Tetrahedron Lett. 2007, 48, 5665.
24. (a) Peterson, D. J.; Logan, T. J. J. Inorg. Nucl. Chem. 1966, 28, 53.
25. (b) Peterson, D. J. US Patent 3 397 039 19680813, 1968; Chem. Abstr. 1968, 69, 60417.
26. (c) Minklei, A. O.; Lecher, H. Z. US Patent 3 397 038 19680813, 1968; Chem. Abstr. 1968, 69, 108219.
27. Jarvis, R. F.; Jacubinas, R. M.; Kaner, R. B. Inorg. Chem. 2000, 39, 3243.
28. (a) Sommerlade, R. H.; Boulmaaz, S.; Wolf, J.-P.; Geier, J.; Gruetzmacher, H.; Scherer, M.; Schoenberg, H.; Stein, D.; Murer, P.; Burkhardt, S. WO Patent 2005014605, A1 20050217, 2005; Chem. Abstr. 2005, 142, 219415.
29. (b) Frank, A. W.; Drake, G. L. Jr. J. Org. Chem. 1971, 36, 3461.
30. 3P seems to be a reasonable assumption, since a 3:1 ratio of the reactants sodium and phosphorus afforded a homogeneous powder in high yield.
31. ( 19) For an observed partial epimerization of 2,5-disubstituted phospholanes upon treatment of corresponding P- phenylphospholanes with lithium, see: Burk, M.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569.
32. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
33. For the synthesis of phosphanes under phase-transfer conditions, see: (a) Lebel, H.; Morin, S.; Paquet, V. Org. Lett. 2003, 5, 2347.
34. (b) Langhans, K. P.; Stelzer, O. Z. Naturforsch., B 1990, 45, 203.
35. For a different protocol to achieve P-alkylation, see: Honaker, M. T.; Sandefur, B. J.; Hargett, J. L.; McDaniel, A. L.; Salvatore, R. N. Tetrahedron Lett. 2003, 44, 8373.
36. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.