Journal of Advanced Medical Sciences and Applied Technologies

Journal of Advanced Medical Sciences and Applied Technologies

Sodium Dodecylphosphonate: An Efficient Anionic Surfactant for the Green Synthesis of α-Hydroxy Phosphonates in Micellar Media

Document Type : Methodology Report

Authors
Soheila Ghassamipour 1
Zahra Fotoohabadi
Nasim Mohammadpour Ghalati
Uranous Niroumand 2
1 Department of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran.
2 Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran.
10.18869/nrip.jamsat.3.1.47
Abstract
A simple and green synthesis of α-hydroxy phosphonates has been performed by reaction between aldehydes and triethyl phosphite using sodium dodecylphosphonate as anionic surfactant in micellar media under reflux conditions. The novel structures were recognized by 1H NMR, 13C NMR and 31P-NMR. The employ of green media, clean reaction profiles, simple experimental and work up procedures and high yields are some of the unique features of this process.
Keywords
Sodium Dodecylphosphonate
Triethylphosphite
α-Hydroxy phosphonates
Micellar media
Benzoxazole
  1. Rosen MJ, Kunjappu JT. Surfactants and interfacial phenomena. New York: John Wiley & Sons; 2012. doi: 10.1002/9781118228920
  2. Rajkumar U, Pokalwar RV, Hangarge PV, Maskeb MS. Synthesis and antibacterial activities of α-hydroxyphosphonates and α-acetyloxyphosphonates derived from 2-chloroquinoline-3-carbaldehyde. Arkivoc. 2006; 2006(11):196. doi: 10.3998/ark.5550190.0007.b20
  3. Rao KUM, Sundar CS, Prasad SS, Rani CR, Reddy CS. Neat synthesis and anti-oxidant activity of α-hydroxyphosphonates. Bulletin of the Korean Chemical Society. 2011; 32(9):3343–7. doi: 10.5012/bkcs.2011.32.9.3343
  4. Gu L, Jin C. Synthesis and antitumor activity of α-aminophosphonates containing thiazole[5,4-b]pyridine moiety. Organic & Biomolecular Chemistry. 2012; 10(35):7098. doi: 10.1039/c2ob25875g
  5. Sobhani S, Tashrifi Z. Synthesis of α-functionalized phosphonates from α-hydroxyphosphonates. Tetrahedron. 2010; 66(7):1429–39. doi: 10.1016/j.tet.2009.11.081
  6. Kafarski P, Lecjzak B. Application of bacteria and fungi as biocatalysts for the preparation of optically active hydroxyphosphonates. Journal of Molecular Catalysis B: Enzymatic. 2004, 29(1-6), 99-104. doi: 10.1016/j.molcatb.2003.12.013
  7. Maly A, Lejczak B, Kafarski P. Quinine as chiral discriminator for determination of enantiomeric excess of diethyl 1,2-dihydroxyalkanephosphonates. Tetrahedron: Asymmetry 2003; 14(8):1019–24. doi: 10.1016/s0957-4166(03)00177-0.
  8. Wynberg H, Smaardijk AA. Asymmetric catalysis in carbon-phosphorus bond formation. Tetrahedron Letters. 1983; 24(52):5899–900. doi: 10.1016/s0040-4039(00)94232-1
  9. Smaardijk AA, Noorda S, van Bolhuis F, Wynberg H. The absolute configuration of α-hydroxyphosphonates. Tetrahedron Letters .1985; 26(4):493–6. doi: 10.1016/s0040-4039(00)61920-2
  10. Akiyama T, Morita H, Itoh J, Fuchibe K. Chiral brønsted acid catalyzed enantioselective hydrophosphonylation of imines: Asymmetric synthesis of α-amino phosphonates. Organic Letters. 2005; 7(13):2583–5. doi: 10.1021/ol050695e
  11. Groaning MD, Rowe BJ, Spilling CD. New homochiral cyclic diol ligands for titanium alkoxide catalyzed phosphonylation of aldehydes. Tetrahedron Letters. 1998; 39(31):5485–8. doi: 10.1016/s0040-4039(98)01139-3
  12. Zhou X, Liu X, Yang X, Shang D, Xin J, Feng X. Highly enantioselective hydrophosphonylation of aldehydes catalyzed by tridentate schiff base aluminum(III) complexes. Angewandte Chemie International Edition. 2008; 47(2):392–4. doi: 10.1002/anie.200704116
  13. Saito B, Katsuki T. synthesis of an optically activec1-symmetric al(salalen) complex and its application to the catalytic hydrophosphonylation of aldehydes. Angewandte Chemie International Edition. 2005; 44(29):4600–2. doi: 10.1002/anie.200501008
  14. Duxbury JP, Cawley A, Thornton-Pett M, Wantz L, Warne JND, Greatrex R, et al. Chiral aluminium complexes as phospho-transfer catalysts. Tetrahedron Letters. 1999; 40(23):4403–6. doi: 10.1016/s0040-4039(99)00738-8
  15. Arai T, Bougauchi M, Sasai H, Shibasaki M. Catalytic asymmetric synthesis of α-hydroxy phosphonates using the al−li−binol complex. The Journal of Organic Chemistry. 1996; 61(9):2926–7. doi: 10.1021/jo960180o
  16. Texier-Boullet F, Lequitte M. ChemInform abstract: An unexpected reactivity of simple heterogeneous mixture of γ-alumina and potassium fluoride: 1-hydroxyalkane phosphonic esters synthesis from non-activated ketones in “dry media”. Chemischer Informationsdienst. 1986; 17(49). doi: 10.1002/chin.198649237
  17. Sonar SS; Kategaonkar AH, Ware MN, Gill CH, Shingate BB, Shingare MS. Ammonium metavanadate: An effective catalyst for synthesis of α-hydroxyphosphonates. Arkivoc. 2009; 2009(2):138. doi: 10.3998/ark.5550190.0010.215
  18. Simoni D, Rondanin R, Morini M, Baruchello R, Invidiata FP. 1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD), 7-methyl-TBD (MTBD) and the polymer-supported TBD (P-TBD): Three efficient catalysts for the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to unsaturated systems. Tetrahedron Letters. 2000; 41(10):1607–10. doi: 10.1016/s0040-4039(99)02340-0
  19. Abell JP, Yamamoto H. Catalytic enantioselective pudovik reaction of aldehydes and Aldimines with tethered bis(8-quinolinato) (TBOx) aluminum complex. Journal of the American Chemical Society. 2008; 130(32):10521–3. doi: 10.1021/ja803859p
  20. Wu Q, Zhou J, Yao Z, Xu F, Shen Q. Lanthanide amides [(Me3Si)2N]3Ln(μ-Cl)Li(THF)3Catalyzed hydrophosphonylation of aryl aldehydes. The Journal of Organic Chemistry. 2010; 75(21):7498–501. doi: 10.1021/jo101743e
  21. Tajbakhsh M, Jahani F, Zamenian B, Khaksar S. Pyridine 2,6-dicarboxylic acid as a bifunctional organocatalyst for hydrophosphonylation of aldehydes and ketones in water. Synthesis. 2010; 2010(19):3315–8. doi: 10.1055/s-0030-1257866
  22. Tajbakhsh M, Heydari A, Khalilzadeh M, Lakouraj M, Zamenian B, Khaksar S. Amberlyst-15 as a heterogeneous reusable catalyst for the synthesis of α-hydroxy phosphonates in water. Synlett. 2007; 2007(15):2347–50. doi: 10.1055/s-2007-985595
  23. Soroka M, Goldeman W. The preparation of dialkyl 1-hydroxyalkylphosphonates in the reaction of trialky phosphites with oxonium salts derived from aldehydes or ketones. Synthesis. 2006; 2006(18):3019–24. doi: 10.1055/s-2006-950200
  24. Reddy N B, Rao K U M, Sundar Ch S , Prasad SS, Nayak S K, Reddy CS. Chitosan catalyzed synthesis and antioxidant activities of diethyl hydroxy (substituted phenyl) methylphosphonates. Organic Communications. 2012; 5(4):171-178.
  25. Ramananarivo HR, Solhy A, Sebti J, Smahi A, Zahouily M, Clark J, et al. An eco-friendly paradigm for the synthesis of α-hydroxyphosphonates using sodium-modified fluorapatite under solventless conditions. ACS Sustainable Chemistry & Engineering. 2013; 1(4):403–9. doi: 10.1021/sc3001417
  26. Naidu KRM, Kumar KS, Arulselvan P, Reddy CB, Lasekan O. Synthesis of α-hydroxyphosphonates and their antioxidant properties. Archiv der Pharmazie. 2012; 345(12):957–63. doi: 10.1002/ardp.201200192
  27. Frings M, Thome I, Schiffers I, Pan F, Bolm C. catalytic, asymmetric synthesis of phosphonic γ-(hydroxyalkyl)butenolides with contiguous quaternary and tertiary stereogen-ic centers. Chemistry-A European Journal. 2014; 20(6):1691–700. doi: 10.1002/chem.201304331
  28. Miao H, Zhou S, Wang S, Zhang L, Wei Y, Yang S, et al. Rare-earth metal amido complexes supported by bridged bis(β-diketiminato) ligand as efficient catalysts for hydrophosphonylation of aldehydes and ketones. Science China Chemistry. 2012; 56(3):329–36. doi: 10.1007/s11426-012-4789-1
Journal of Advanced Medical Sciences and Applied Technologies
Volume 3, Issue 1 - Serial Number 1
11
March 2017
Pages 47-51