A Methodology Study of Hydrophosphonylation of Aldehydes Derivatives with H6P2W18O62·14H2O as a Catalyst

Aouf, Zineb; Boughaba, Sara; Lakrout, Salah; Bechiri, Ouahiba; Aouf, Nour-Eddine

doi:doi.org/10.23939/chcht14.02.154

Please use this identifier to cite or link to this item: https://oldena.lpnu.ua/handle/ntb/55795

Title:	A Methodology Study of Hydrophosphonylation of Aldehydes Derivatives with H6P2W18O62·14H2O as a Catalyst
Other Titles:	Методологія дослідження гідрофосфонілювання альдегідних похідних з H6P2W18O62·14H2O, як відновлювального каталізатора
Authors:	Aouf, Zineb Boughaba, Sara Lakrout, Salah Bechiri, Ouahiba Aouf, Nour-Eddine
Affiliation:	Badji Mokhtar-Annaba University
Bibliographic description (Ukraine):	A Methodology Study of Hydrophosphonylation of Aldehydes Derivatives with H6P2W18O62·14H2O as a Catalyst / Zineb Aouf, Sara Boughaba, Salah Lakrout, Ouahiba Bechiri, Nour-Eddine Aouf // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2020. — Vol 14. — No 2. — P. 154–160.
Bibliographic description (International):	A Methodology Study of Hydrophosphonylation of Aldehydes Derivatives with H6P2W18O62·14H2O as a Catalyst / Zineb Aouf, Sara Boughaba, Salah Lakrout, Ouahiba Bechiri, Nour-Eddine Aouf // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2020. — Vol 14. — No 2. — P. 154–160.
Is part of:	Chemistry & Chemical Technology, 2 (14), 2020
Issue:	2
Volume:	14
Issue Date:	24-Jan-2020
Publisher:	Видавництво Львівської політехніки Lviv Politechnic Publishing House
Place of the edition/event:	Львів Lviv
DOI:	doi.org/10.23939/chcht14.02.154
Keywords:	альдегід діетилфосфіт реакція Пудовика α-гідроксифосфонат aldehyde diethylphosphite Pudovik reaction α-hydroxyphosphonate
Number of pages:	7
Page range:	154-160
Start page:	154
End page:	160
Abstract:	Розроблено каталітичний процес гідрофонфонілювання альдегідів загальної формули H6P2W18O62·14H2O. Для отримання α-гідроксифосфонатів різні альдегіди піддавали взаємодії з діетилфосфітом у присутності 1 % гетерополікислоти як каталізатора. Синтезовані сполуки охарактеризовані за допомогою ІЧ-спектроскопії та методів 1Н ЯМР, 13С ЯМР і 31P ЯМР. Показано, що головною перевагою розробленого процессу є прості та м‘які умови синтезу, незначний час реакції, відсутність розчинників, доступність та можливість відновлення каталізатора. A catalytic process for hydrophosphonylation of aldehydes with H6P2W18O62·14H2O has been developed in this paper. Various aldehydes were reacted with diethylphosphite in the presence of 1 % of heteropolyacids (HPAs) as a catalyst to generate the α-hydroxyphosphonates. All the synthesized compounds were sys tematically characterized by IR, 1H NMR, 13C NMR, and 31P NMR. Simple and mild method, short reaction time, solvent-free conditions, availability and reusability of the catalyst are the main advantages of this procedure
URI:	https://ena.lpnu.ua/handle/ntb/55795
Copyright owner:	© Національний університет “Львівська політехніка”, 2020 © Aouf Z., Boughaba S., Lakrout S., Bechiri O., Aouf N.-E., 2020
URL for reference material:	https://doi.org/10.1210/edrv.19.1.0325 https://doi.org/10.1002/ardp.201200192 https://doi.org/10.1016/j.molcatb.2003.12.013 https://doi.org/10.1021/jm980325e https://doi.org/10.1016/S0040-4020(99)00681-X https://doi.org/10.1016/S0040-4039(02)02727-2 https://doi.org/10.1055/s-2004-829124 https://doi.org/10.1081/SCC-120030697 https://doi.org/10.1016/S0040-4020(99)00037-X https://doi.org/10.1021/ja01110a508 https://doi.org/10.1080/10426500008082399 https://doi.org/10.1016/S0040-4039(00)61920-2 https://doi.org/10.1055/s-2007-985595 https://doi.org/10.1021/jo00109a025 https://doi.org/10.1021/ja0651005 https://doi.org/10.1016/S0040-4039(00)84837-6 https://doi.org/10.1016/j.catcom.2008.07.005 https://doi.org/10.1055/s-1982-29888 https://doi.org/10.1002/hc.20649 https://doi.org/10.1039/C0GC00026D https://doi.org/10.1080/10426500211718 https://doi.org/10.1080/00397919708003324 https://doi.org/10.1080/10426507.2013.843002 https://doi.org/10.1002/hc.20304 https://doi.org/10.1021/jo01076a035 https://doi.org/10.1021/ja062091r https://doi.org/10.1007/s1116 https://doi.org/10.1039/C5RA03473F https://doi.org/10.2174/1385272822666180404145804 https://doi.org/10.5012/bkcs.2011.32.9.3343 https://doi.org/10.1016/S02775387(00)84366-1 https://doi.org/10.1039/C3OB40767E https://doi.org/10.1080/00397911.2010.523492 https://doi.org/10.1002/anie.200704116 https://doi.org/10.1080/10426507.2016.1247085
References (Ukraine):	[1] Corbridge D.: Phosphorus: An Outline of its Chemistry, Biochemistry and Technology, 5th edn. Elsevier, Amesterdam 1995. [2] Francis M., Martodam R.: Chemical, Biochemical and Medicinal Properties of the Diphosphonates [in:] Hilderbrand R. (Ed), The Role of Phosphonates in Living Systems. CRC Press, Boca Raton 1983, 55. [3] Neyts J., De Clercq E.: Antimicrob. Agents Chemother., 1997, 41, 2754. [4] Lee M., Fong E., Singer F., Guenette R.: Cancer. Res., 2001, 61, 2602. [5] Fleisch H.: Endocr. Rev., 1998, 19, 80. https://doi.org/10.1210/edrv.19.1.0325 [6] Naidu K., Kumar K., Arulselvan P. et al.: Arch. Pharm., 2012, 345, 957. https://doi.org/10.1002/ardp.201200192 [7] Kafarski P., Lejczak B.:J. Mol. Catal. B, 2004, 29, 99. https://doi.org/10.1016/j.molcatb.2003.12.013 [8] Tao M., BihovskyR., Wells G., Mallamo J.:J. Med. Chem., 1998, 41, 3912. https://doi.org/10.1021/jm980325e [9] Zheng X., Nair V.: Tetrahedron, 1999, 55, 11803. https://doi.org/10.1016/S0040-4020(99)00681-X [10] Kaboudin B.: Tetrahedron Lett., 2003, 44, 1051. https://doi.org/10.1016/S0040-4039(02)02727-2 [11] Firouzabadi H., Iranpoor N., Sobhani S., Amoozgar Z.: Synthesis, 2004, 11, 1771. https://doi.org/10.1055/s-2004-829124 [12] Firouzabadi H., Iranpoor N., Sobhani S.: Synth. Commun., 2004, 34, 1463. https://doi.org/10.1081/SCC-120030697 [13] Lorga B., Eymery F., Savignac P.: Tetrahedron, 1999, 55, 2671. https://doi.org/10.1016/S0040-4020(99)00037-X [14] Abramov V.: Dokl. Akad. Nauk SSSR, 1950, 73, 487. [15] Pudovik A., Arbuzov B.: Dokl. Akad. Nauk SSSR, 1950, 73, 327. [16] Gawron O., Grelecki C., Reilly W., SandsJ.:J. Am. Chem. Soc., 1953, 75, 3591. https://doi.org/10.1021/ja01110a508 [17] Kumar K., ReddyC., Reddy M. et al.: Org. Commun., 2012, 5, 50. [18] Alexander C., Albiniak P., Gibson L.: Phosphorus Sulfur, 2000, 167, 205. https://doi.org/10.1080/10426500008082399. [19] Smaardijk A., Noorda S., Bolhuis F.,Wynberg H.: Tetrahedron Lett., 1985, 26, 493. https://doi.org/10.1016/S0040-4039(00)61920-2 [20] Tajbakhsh M., Heydari A., Khalizadeh M. et al.: Synlett., 2007, 15, 2347. https://doi.org/10.1055/s-2007-985595 [21] Blazis V., Koeller K., Spilling C.:J. Org. Chem., 1995, 60, 931. https://doi.org/10.1021/jo00109a025 [22] Saito B., Egami H., Katsuki T.:J. Am. Chem.Soc., 2007, 129, 1978. https://doi.org/10.1021/ja0651005 [23] Textier-Boullet F., Lequitte M.: Tetrahedron. Lett., 1986, 27, 3515. https://doi.org/10.1016/S0040-4039(00)84837-6 [24] Smahi A., Solhy A., Tahir R. et al.: Catal. Commun., 2008, 9, 2503.https://doi.org/10.1016/j.catcom.2008.07.005 [25] Baraldi P., Guarnieri M., Moroder F. et al.: Synthesis, 1982, 8, 653. https://doi.org/10.1055/s-1982-29888 [26] Keglevich G.,Toth V., Drahos L.: Heteroatom. Chem., 2011, 22, 15. https://doi.org/10.1002/hc.20649 [27] Martinez-Castro E., Lopez O., Maya I. et al.: Green Chem., 2010, 12, 1171. https://doi.org/10.1039/C0GC00026D [28]Jeanmaire T., Hervaud Y., Boutevin B.: Phosphorus Sulfur, 2002, 177, 1137. https://doi.org/10.1080/10426500211718 [29] Sardarian A., Kaboudin B.: Synth. Commun., 1997, 27, 543. https://doi.org/10.1080/00397919708003324 [30] Rasheed S., Venkata Ramana K., Madhava G. et al.: Phosphorus Sulfur, 2014, 189, 606. https://doi.org/10.1080/10426507.2013.843002 [31] Feng D.,Chen R.,Huang Y., Song H.: Heteroatom. Chem., 2007, 18, 347. https://doi.org/10.1002/hc.20304 [32] Kharasch M., Mosher R., Bengelsdorf I.:J. Org. Chem., 1960, 25, 1000. https://doi.org/10.1021/jo01076a035 [33] Samanta S.,Zhao C.:J. Am. Chem. Soc., 2006, 128, 7442. https://doi.org/10.1021/ja062091r [34] Pope M.: Heteropoly and IsopolyOxometalates. Springer Verlag, NewYork 1983. [35] Bouzina A., Aouf N., Berredjem M.: Res. Chem. Intermed., 2016, 42, 5993. https://doi.org/10.1007/s1116 [36] Belhani B., Berredjem M., Le Borgne M. et al.: RSC Adv., 2015, 5, 39324. https://doi.org/10.1039/C5RA03473F [37] Boughaba S., Bouacida S., Aouf Z. et al.: Curr. Org. Chem, 2018, 22, 1335. https://doi.org/10.2174/1385272822666180404145804 [38] Rao U., Sundar S., Prasad S. et al.: Bull. Korean Chem. Soc., 2011, 32, 3343. https://doi.org/10.5012/bkcs.2011.32.9.3343 [39] Ciabrini J.,Contant R., Fruchart J.: Polyhedron,1983, 2, 1229. https://doi.org/10.1016/S02775387(00)84366-1 [40] Angelini T., Bonollo S., Lanari D. et al.: Org. Biomol. Chem., 2013, 11, 5042. https://doi.org/10.1039/C3OB40767E [41] Ramesh K., Madhav B., Murthy S., NageswarY.: Synth. Commun., 2012, 42, 258. https://doi.org/10.1080/00397911.2010.523492 [42] Zhou X., Liu X., Yang X. et al.: Angew. Chem. Int. Ed., 2008, 47, 392. https://doi.org/10.1002/anie.200704116 [43] Kumar A., Jamwal S., Khan S. et al.: Phosphorus Sulfur, 2017, 192, 381. https://doi.org/10.1080/10426507.2016.1247085
References (International):	[1] Corbridge D., Phosphorus: An Outline of its Chemistry, Biochemistry and Technology, 5th edn. Elsevier, Amesterdam 1995. [2] Francis M., Martodam R., Chemical, Biochemical and Medicinal Properties of the Diphosphonates [in:] Hilderbrand R. (Ed), The Role of Phosphonates in Living Systems. CRC Press, Boca Raton 1983, 55. [3] Neyts J., De Clercq E., Antimicrob. Agents Chemother., 1997, 41, 2754. [4] Lee M., Fong E., Singer F., Guenette R., Cancer. Res., 2001, 61, 2602. [5] Fleisch H., Endocr. Rev., 1998, 19, 80. https://doi.org/10.1210/edrv.19.1.0325 [6] Naidu K., Kumar K., Arulselvan P. et al., Arch. Pharm., 2012, 345, 957. https://doi.org/10.1002/ardp.201200192 [7] Kafarski P., Lejczak B.:J. Mol. Catal. B, 2004, 29, 99. https://doi.org/10.1016/j.molcatb.2003.12.013 [8] Tao M., BihovskyR., Wells G., Mallamo J.:J. Med. Chem., 1998, 41, 3912. https://doi.org/10.1021/jm980325e [9] Zheng X., Nair V., Tetrahedron, 1999, 55, 11803. https://doi.org/10.1016/S0040-4020(99)00681-X [10] Kaboudin B., Tetrahedron Lett., 2003, 44, 1051. https://doi.org/10.1016/S0040-4039(02)02727-2 [11] Firouzabadi H., Iranpoor N., Sobhani S., Amoozgar Z., Synthesis, 2004, 11, 1771. https://doi.org/10.1055/s-2004-829124 [12] Firouzabadi H., Iranpoor N., Sobhani S., Synth. Commun., 2004, 34, 1463. https://doi.org/10.1081/SCC-120030697 [13] Lorga B., Eymery F., Savignac P., Tetrahedron, 1999, 55, 2671. https://doi.org/10.1016/S0040-4020(99)00037-X [14] Abramov V., Dokl. Akad. Nauk SSSR, 1950, 73, 487. [15] Pudovik A., Arbuzov B., Dokl. Akad. Nauk SSSR, 1950, 73, 327. [16] Gawron O., Grelecki C., Reilly W., SandsJ.:J. Am. Chem. Soc., 1953, 75, 3591. https://doi.org/10.1021/ja01110a508 [17] Kumar K., ReddyC., Reddy M. et al., Org. Commun., 2012, 5, 50. [18] Alexander C., Albiniak P., Gibson L., Phosphorus Sulfur, 2000, 167, 205. https://doi.org/10.1080/10426500008082399. [19] Smaardijk A., Noorda S., Bolhuis F.,Wynberg H., Tetrahedron Lett., 1985, 26, 493. https://doi.org/10.1016/S0040-4039(00)61920-2 [20] Tajbakhsh M., Heydari A., Khalizadeh M. et al., Synlett., 2007, 15, 2347. https://doi.org/10.1055/s-2007-985595 [21] Blazis V., Koeller K., Spilling C.:J. Org. Chem., 1995, 60, 931. https://doi.org/10.1021/jo00109a025 [22] Saito B., Egami H., Katsuki T.:J. Am. Chem.Soc., 2007, 129, 1978. https://doi.org/10.1021/ja0651005 [23] Textier-Boullet F., Lequitte M., Tetrahedron. Lett., 1986, 27, 3515. https://doi.org/10.1016/S0040-4039(00)84837-6 [24] Smahi A., Solhy A., Tahir R. et al., Catal. Commun., 2008, 9, 2503.https://doi.org/10.1016/j.catcom.2008.07.005 [25] Baraldi P., Guarnieri M., Moroder F. et al., Synthesis, 1982, 8, 653. https://doi.org/10.1055/s-1982-29888 [26] Keglevich G.,Toth V., Drahos L., Heteroatom. Chem., 2011, 22, 15. https://doi.org/10.1002/hc.20649 [27] Martinez-Castro E., Lopez O., Maya I. et al., Green Chem., 2010, 12, 1171. https://doi.org/10.1039/P.0GC00026D [28]Jeanmaire T., Hervaud Y., Boutevin B., Phosphorus Sulfur, 2002, 177, 1137. https://doi.org/10.1080/10426500211718 [29] Sardarian A., Kaboudin B., Synth. Commun., 1997, 27, 543. https://doi.org/10.1080/00397919708003324 [30] Rasheed S., Venkata Ramana K., Madhava G. et al., Phosphorus Sulfur, 2014, 189, 606. https://doi.org/10.1080/10426507.2013.843002 [31] Feng D.,Chen R.,Huang Y., Song H., Heteroatom. Chem., 2007, 18, 347. https://doi.org/10.1002/hc.20304 [32] Kharasch M., Mosher R., Bengelsdorf I.:J. Org. Chem., 1960, 25, 1000. https://doi.org/10.1021/jo01076a035 [33] Samanta S.,Zhao C.:J. Am. Chem. Soc., 2006, 128, 7442. https://doi.org/10.1021/ja062091r [34] Pope M., Heteropoly and IsopolyOxometalates. Springer Verlag, NewYork 1983. [35] Bouzina A., Aouf N., Berredjem M., Res. Chem. Intermed., 2016, 42, 5993. https://doi.org/10.1007/s1116 [36] Belhani B., Berredjem M., Le Borgne M. et al., RSC Adv., 2015, 5, 39324. https://doi.org/10.1039/P.5RA03473F [37] Boughaba S., Bouacida S., Aouf Z. et al., Curr. Org. Chem, 2018, 22, 1335. https://doi.org/10.2174/1385272822666180404145804 [38] Rao U., Sundar S., Prasad S. et al., Bull. Korean Chem. Soc., 2011, 32, 3343. https://doi.org/10.5012/bkcs.2011.32.9.3343 [39] Ciabrini J.,Contant R., Fruchart J., Polyhedron,1983, 2, 1229. https://doi.org/10.1016/S02775387(00)84366-1 [40] Angelini T., Bonollo S., Lanari D. et al., Org. Biomol. Chem., 2013, 11, 5042. https://doi.org/10.1039/P.3OB40767E [41] Ramesh K., Madhav B., Murthy S., NageswarY., Synth. Commun., 2012, 42, 258. https://doi.org/10.1080/00397911.2010.523492 [42] Zhou X., Liu X., Yang X. et al., Angew. Chem. Int. Ed., 2008, 47, 392. https://doi.org/10.1002/anie.200704116 [43] Kumar A., Jamwal S., Khan S. et al., Phosphorus Sulfur, 2017, 192, 381. https://doi.org/10.1080/10426507.2016.1247085
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