Novel synthesis of phosphinates by the microwave-assisted esterification of phosphinic acids

Synthetic Communications

Volumn 39, Issue 13, 2009, Pages 2392-2404

  Kiss, Nóra Zsuzsa ^a   Ludányi, Krisztina ^b,c   Drahos, László ^c   Keglevich, György ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b SEMMELWEIS UNIVERSITY   (Hungary)

^c CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

Esterification; Green chemistry; Microwave synthesis; Phosphinates; Phosphinic acids

Indexed keywords

(1 BUTOXY) 3 METHYL 3 PHOSPHOLENE 1 OXIDE; 1 HYDROXY 3 PHOSPHOLENE OXIDE DERIVATIVE; ALCOHOL DERIVATIVE; DIPHENYLPHOSPHINIC ACID; PHENYL H PHOSPHINIC ACID; PHOSPHINATE DERIVATIVE; PHOSPHINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ESTERIFICATION; HEATING; MASS SPECTROMETRY; MICROWAVE IRRADIATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; STEREOSPECIFICITY; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 67650284498     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802654880     Document Type: Article

References (37)

1. Edmundson, R. S. Phosphoric acid derivatives. In Comprehensive Organic Chemistry; D. Barton, D. Ollis, I. O. Sutherland (Eds.); Pergamon: Oxford, 1979; vol. 2. ch. 10.5, p. 1291.
2. Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000.
3. Harger, M. J. P.; Westlake, S. Diarylphosphinic azides-Photochemical- reactions including rearrangement in methanol. Tetrahedron 1982, 38, 1511-1515.
4. Andrianov, K. A.; Kuznetsova I. K. Reactions of chloromethylmethyldialkoxysilanes with sodium salts of diethylphosphoric and dimethylphosphinic acids. Izv. Akad. Nauk SSSR, Otdel. Khim. Nauk 1961, 1454-1456.
5. Godovikov, N. N.; Kardanov, N. A.; Chepaikina, T. A.; Kabachnik, M. I. Synthesis of some N-substituted β-aminoethyl esters of α- hydroxoyphosphonic acids and their methiodides. Izv. Akad. Nauk SSSR, Ser. Khim. 1981, 2824-2828.
6. Golubski, Z. E. Alkylation of phosphinic acid salts in the presence of crown ethers. Synthesis 1980, 632-634.
7. Tanaka, M.; Hua, R. Method for preparation of phosphinic acid alkenyl esters by catalytic esterification of phosphinic acids with terminal acetylene compounds. JP 11180990 A, 1999.
8. Bravo-Altamirano, K.; Huang, Z.; Montchamp, J.-L. Palladium-catalyzed phosphorus-carbon bond formation: Cross-coupling reactions of alkyl phosphinates with aryl, heteroaryl, alkenyl, benzylic, and allylic halides and triflates. Tetrahedron 2005, 61, 6315-6329.
9. Fitch, S. J. Synthesis of hypophosphite esters from orthocarbonyl compounds. J. Am. Chem. Soc. 1964, 86, 61-64.
10. Schwabacher, A. W.; Stefanescu, A. D. Improved preparation of phosphinate esters for palladium-catalyzed cross-coupling. Tetrahedron Lett. 1996, 37, 425-428.
11. Yoshino, T.; Imori, S.; Togo, H. Efficient esterification of carboxylic acids and phosphonic acids with trialkyl orthoacetate in ionic liquid. Tetrahedron 2006, 62, 1309-1317.
12. Afarinkia, K.; Yu, H.-W. Hewitt reaction revisited. Tetrahedron Lett. 2003, 44, 781-783.
13. Depre'le, S.; Montchamp, J.-L. A novel and convenient preparation of hypophosphite esters. J. Organomet. Chem. 2002, 643=644, 154-163.
14. Dumond, Y. R.; Baker, R. L.; Montchamp, J.-L. Orthosilicate-mediated esterification of monosubstituted phosphinic acids. Org. Lett. 2000, 2, 3341-3344.
15. Berezovskaya, I. V.; Eliseeva, L. A.; Kuznetsov, E. V.; Mukhametzyanova, E. K.; Shermergorn, I. M. Synthesis and study of properties of bis(allyloxymethyl) phosphinic acid and its esters. Izv. Akad. Nauk SSSR, Ser. Khim. 1968, 1369-1371.
16. Markowska, A.; Olejnik, J.; Michalski, J. Selective alkylation of polybasic phosphoric acids with trialkyl phosphite. Chem. Ber. 1975, 108, 2589-2592.
17. Hopkins, T. R.; Vogel, P. W. Aromatic phosphinic acids and derivatives, II: Direct esterification of diphenylphosphinodithioic acid. J. Am. Chem. Soc. 1956, 78, 4447-4450.
18. Keglevich, G.; Novák, T.; Vida, L.; Greiner, I. Microwave irradiation as an alternative to phase transfer catalysis in the liquid-solid phase, solvent-free C-alkylation of active methylene containing substrates. Green Chem. 2006, 8, 1073-1075.
19. Keglevich, G.; Majrik, K.; Vida, L.; Greiner, I. Microwave irradiation as a green alternative to phase transfer catalysis: Solid-liquid phase alkylation of active methylene containing substrates under solvent-free conditions. Lett. Org. Chem. 2008, 5, 224-228.
20. Keglevich, G.; Bálint, E.; Karsai, E' .; Grü n, A.; Bálint, M.; Greiner, I. Chemoselectivity in the microwave-assisted solvent-free solid-liquid phase benzylation of phenols: O- versus C-alkylation. Tetrahedron Lett. 2008, 49, 5039-5042.
21. Keglevich, G.; Dudás, E.; Sipos, M.; Lengyel, D.; Ludányi, K. Efficient synthesis of cyclic β-oxophosphoranes by the microwave-assisted reaction of cyclic phosphine oxides and dialkyl acetylenedicarboxylate. Synthesis 2006, 1365-1369.
22. Prauda, I.; Greiner, I.; Ludányi, K.; Keglevich, G. Efficient synthesis of phosphono- and phosphinoxidomethylated N-heterocycles under solvent-free microwave conditions. Synth. Commun. 2007, 37, 317-322.
23. Keglevich, G.; Szekre'nyi, A.; Sipos, M.; Ludányi, K.; Greiner, I. Synthesis of cyclic aminomethylphosphonates and aminomethyl-arylphosphinic acids by an efficient microwave-mediated phospha-Mannich approach. Heteroatom Chem. 2008, 19, 207-210.
24. Mathey, F. (Ed.). Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain; Pergamon: Amsterdam, 2001.
25. Hasserodt, U.; Hunger, K.; Korte, F. Phospholin-derivate aus phosphortrihalogeniden und dienen. Tetrahedron 1963, 19, 1563-1575.
26. Keglevich, G.; Brlik, J.; Janke, F.; T}oke, L. Convenient synthesis of 1-alkoxy-1,2-dihydrophosphinine 1-oxides by ring enlargement. Heteroatom Chem. 1990, 1, 419-424.
27. Keglevich, G.; T}oke, L.; Kovács, A.; Táth, G.; U' jszászy, K. Convenient synthesis of 1-alkoxy-di- and tetrahydrophosphinine 1-oxides by ring enlargement. Heteroatom Chem. 1993, 4, 61-72.
28. Cherbuliez, E.; Weber, G.; Rabinowitz, J. Formation and transformation of esters, XLVII: Monoesters of various acids of phosphorus and their rate of hydrolysis at different pH values. Helv. Chim. Acta 1963, 46, 2464-2471.
29. Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. J. Radical addition reactions of phosphorus hydrides: Tuning the reactivity of phosphorus hydrides, the use of microwaves and Horner-Wadsworth-Emmons-type reactions. Eur. J. Org. Chem. 2006, 1547-1554.
30. Arbusov, B. A.; Vizel, A. O. Cyclic trihalophosphoranes and some of their transformations: Synthesis from phosphorus trichloride. Dokl. Akad. Nauk SSSR 1964, 158, 1105-1108.
31. Kabachnik, M. I.; Tsvetkov, E. N.; Chang, C.-Y. A method of synthesis of acid esters of phosphinic acids. Dokl. Akad. Nauk SSSR 1959, 125, 1260-1262.
32. Bochwic, B.; Michalski, J. Studies on organic phosphorus compounds II: Addition of alkyl arylphosphinates to ethylenic derivatives. Roczniki Chemii 1952, 26, 593-603.
33. Bravo-Altamirano, K.; Huang, Z.; Montchamp, J.-L. Palladium-catalyzed phosphorus-carbon bond formation: Cross-coupling reactions of alkyl phosphinates with aryl, heteroaryl, alkenyl, benzylic, and allylic halides and triflates. Tetrahedron 2005, 61, 6315-6329.
34. Pudovik, A. N.; Yarmukhametova, D. K. New synthesis of esters of phosphonic and thiophosphonic acids, XV: Addition of esters of phenyland alkylphosphonous acids to esters of methacrylic and acrylic acids. Izv. Akad. Nauk SSSR, Ser Khim. 1952, 902-907.
35. Dahn, H.; Toan, V. V.; Ung-Truong, M.-N. 9'-17O NMR of the P-O "double bond": Phosphine oxides, phosphinates, phosphonates, acylphosphonates, and related compounds. Magn. Reson. Chem. 1992, 30, 1089-1096.
36. Afarinkia, K.; Yu, H.-W. Hewitt reaction revisited. Tetrahedron Lett. 2003, 44, 781-783.
37. Xu, Y.; Li, Z.; Xia, J.; Guo, H.; Huang, Y. Palladium-catalysed synthesis of unsymmetrical alkyl aryl-phenylphosphinates. Synthesis 1983, 377-378.