Synthesis 2020; 52(15): 2224-2232
DOI: 10.1055/s-0040-1707945
paper
© Georg Thieme Verlag Stuttgart · New York

Catalyst- and Solvent-Free Hydrophosphorylation of Ketones with Secondary Phosphine Oxides: Green Synthesis of Tertiary α-Hydroxyphosphine Oxides

Nina K. Gusarova
,
Nina I. Ivanova
,
Kseniya O. Khrapova
,
Pavel A. Volkov
,
Anton A. Telezhkin
,
Lyudmila I. Larina
,
Andrei V. Afonin
,
Dmitry V. Pavlov
,
Boris A. Trofimov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   eMail: boris_trofimov@irioch.irk.ru
› Institutsangaben
This work has been approved by plans for research projects at the IPC RAS State, Registration No. AAAA-A16-116112510005-7.
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Publikationsverlauf

Received: 14. Februar 2020

Accepted after revision: 06. April 2020

Publikationsdatum:
22. April 2020 (online)


Abstract

Tertiary α-hydroxyphosphine oxides have been synthesized via the catalyst- and solvent-free reaction between available secondary phosphine oxides and aliphatic, aromatic and heteroaromatic ketones at 20–62 °C in near to 96–98% yield. The developed method meets the requirements of green chemistry and the PASE (pot, atom, step economy) paradigm. According to quantum-chemical calculations at the B3LYP/6-311++G(d,p) level, the synthesized hydroxyphosphine oxides feature a weak (≈3 kcal·mol–1) O−H···O=P intramolecular hydrogen bond.

Supporting Information

 
  • References

    • 1a Chandrasekharan P, Yong C.-X, Poh Z, He T, He Z, Liu S, Robins EG, Chuang K.-H, Yang C.-T. Biomaterials 2012; 33: 9225
    • 1b Shaikh TM, Weng C.-M, Hong F.-E. Coord. Chem. Rev. 2012; 256: 771
    • 1c Rummelt SM, Ranocchiari M, van Bokhoven JA. Org. Lett. 2012; 14: 2188
    • 1d Neuwald B, Oelscher F, Goettker-Schnetmann I, Mecking S. Organometallics 2012; 31: 3128
    • 1e Sun W, Yu J, Deng R, Rong Y, Fujimoto B, Wu C, Zhang H, Chiu DT. Angew. Chem. Int. Ed. 2013; 52: 11294
    • 1f Gowrisankar S, Neumann H, Goerdes D, Thurow K, Jiao H, Beller M. Chem. Eur. J. 2013; 19: 15979
    • 1g Tay WS, Yang X.-Y, Li Y, Pullarkat SA, Leung P.-H. RSC Adv. 2016; 6: 75951
    • 1h Bannister RD, Levason W, Light ME, Reid G. Polyhedron 2018; 154: 259
    • 2a Alguacil FJ, Alonso M. Hydrometallurgy 2004; 74: 157
    • 2b Flett DS. J. Organomet. Chem. 2005; 690: 2426
    • 2c Banerjee S, Basu S. J. Indian Chem. Soc. 2005; 82: 1035
    • 2d Atanassova M, Kaloyanova S, Deligeorgiev T. Acta Chim. Slov. 2010; 57: 821
    • 2e Petrova MA, Kurteva VB, Lubenov LA. Ind. Eng. Chem. Res. 2011; 50: 12170
    • 2f Roy S, Basu S. J. Indian Chem. Soc. 2015; 92: 1199
    • 3a Liu H, Owen JS, Alivisatos AP. J. Am. Chem. Soc. 2007; 129: 305
    • 3b Loubiri D, Ben Hamed Z, Ilahi S, Sanhoury MA, Kouki F, Yacoubi N. Synth. Met. 2015; 206: 1
    • 3c Benchaabane A, Ben Hamed Z, Sanhoury MA, Kouki F, Zeinert A, Bouchriha H. Appl. Phys. 2016; 122: 60
    • 4a Price D, Pyrah K, Cunliffe LK, Hull TR, Milnes GJ, Ebdon JR, Hunt BJ, Joseph P. Rec. Adv. Flame Retard. Polym. Mater. 2001; 12: 1
    • 4b Howell BA, Carter KE. J. Therm. Anal. Calorim. 2010; 102: 493
    • 4c Chen M.-J, Chen C.-R, Tan Y, Huang J.-Q, Wang X.-L, Chen L, Wang Y.-Z. Ind. Eng. Chem. Res. 2014; 53: 1160
  • 5 Moiseev DV, James BR, Hu TQ. Phosphorus, Sulfur Silicon Relat. Elem. 2012; 187: 433
    • 6a Cristau HJ, Brahic C, Pirat JL. Tetrahedron 2001; 57: 9149
    • 6b Nawrot B, Michalak O, Clercq ED, Stec WJ. Antivir. Chem. Chemother. 2004; 15: 319
    • 6c Stroman DW, Chowhan MA, Schneider LW, Bartell JG, Han WW. Patent PCT Int. Appl. WO 2010091280 A1, 2010
    • 6d Alexandre F.-R, Amador A, Bot S, Caillet C, Convard T, Jakubik J, Musiu C, Poddesu B, Vargiu L, Liuzzi M, Roland A, Seifer M, Standring D, Storer R, Dousson CB. J. Med. Chem. 2011; 54: 392
    • 6e Olsson RI, Jacobson I, Boström J, Fex T, Björe A, Olsson C, Sundell J, Gran U, Öhrn A, Nordin A, Gyll J, Thorstensson M, Hayen A, Aplander K, Hidestal O, Jiang F, Linhardt G, Forsström E, Collins T, Sundqvist M, Lindhardt E, Astrand A, Löfberg B. Bioorg. Med. Chem. Lett. 2013; 23: 706
    • 7a Herd O, Hebler A, Hingst M, Machnitzki P, Terrer M, Stelzer O. Catal. Todаy 1998; 42: 413
    • 7b Gusarova NK, Ivanova NI, Volkov PA, Larina LI. Synthesis 2008; 3525
    • 7c Ivanova NI, Volkov PA, Khrapova KO, Larina LI, Bagryanskaya IYu, Gusarova NK, Trofimov BA. Russ. J. Org. Chem. 2016; 52: 772
    • 7d Jia K, Li J, Chen Y. Chem. Eur. J. 2018; 24: 3174
    • 8a Gusarova NK, Reutskaya AM, Ivanova NI, Medvedeva AS, Demina MM, Novopashin PS, Afonin AV, Albanov AI, Trofimov BA. J. Organomet. Chem. 2002; 659: 172
    • 8b Ivanova NI, Gusarova NK, Nikitina EA, Albanov AI, Sinegovskaya LM, Nikitin MV, Konovalova NA, Trofimov BA. Phosphorus, Sulfur Silicon Relat. Elem. 2004; 179: 7
    • 8c Priya S, Balakrishna MS, Mobin SM. Polyhedron 2005; 24: 1641
    • 8d Yuan X.-L, Liu W.-Y, Huo P, Mei G.-O. Acta Crystallogr., Ser. E 2010; 66: 2331
    • 8e Keglevich G, Tóth VR, Drahos L. Heteroat. Chem. 2011; 22: 15
    • 8f Gusarova NK, Ivanova NI, Volkov PA, Khrapova KO, Larina LI, Smirnov VI, Borodina TN, Trofimov BA. Synthesis 2015; 47: 1611
    • 9a Pudovik AN, Konovalova IV. Synthesis 1979; 81
    • 9b Goerlich JR, Schmutzler R. Phosphorus, Sulfur Silicon Relat. Elem. 1995; 101: 213
    • 9c Odinets IL, Matveeva EV. Curr. Org. Chem. 2010; 14: 1171
    • 9d Zheng J, Feng X, Yu Y, Zhen X, Zhao Yu. Phosphorus, Sulfur Silicon Relat. Elem. 2013; 188: 1080
    • 9e Guin J, Wang Q, van Gemmeren M, List B. Angew. Chem. Int. Ed. 2015; 54: 355
    • 9f Kiss NZ, Radai Z, Musci Z, Keglevich G. Heteroat. Chem. 2016; 27: 260
    • 9g Keglevich G, Radai Z, Kiss NZ. Green Process Synth. 2017; 6: 197
    • 9h Cytlak T, Skibińska M, Kaczmarek P, Kaźmierczak M, Rapp M, Kubickia M, Koroniak H. RSC Adv. 2018; 8: 11957
    • 9i Koszelewski D, Ostaszewski R. ChemCatChem 2019; 11: 2554
    • 10a Well М, Schmutzler R. Phosphorus 1992; 72: 171
    • 10b Goerlich JR, Plack V, Schmutzler R. J. Fluorine Chem. 1996; 76: 29
    • 10c Dvorko MYu, Glotova TE, Ushakov IA, Gusarova NK. Russ. J. Org. Chem. 2010; 46: 485
    • 11a Alonso F, Moglie Y, Radivoy G, Yus M. Green Chem. 2012; 14: 2699
    • 11b Alonso F, Moglie Y. Curr. Green Chem. 2014; 1: 87
    • 11c Malysheva SF, Gusarova NK, Artem’ev AV, Belogorlova NA, Albanov AI, Borodina TN, Smirnov VI, Trofimov BA. Synthesis 2014; 46: 2656
    • 11d Malysheva SF, Artem’ev AV, Gusarova NK, Belogorlova NA, Albanov AI, Liu CW, Trofimov BA. Beilstein J. Org. Chem. 2015; 11: 1985
    • 11e Artem’ev AV, Malysheva SF, Gusarova NK, Belogorlova NA, Shagun VA, Albanov AI, Trofimov BA. Synthesis 2015; 47: 263
    • 11f Moglie Y, González-Soria MJ, Martín-García I, Radivoy G, Alonso F. Green Chem. 2016; 18: 4896
    • 11g Gusarova NK, Chernysheva NA, Trofimov BA. Synthesis 2017; 49: 4783
    • 12a Trofimov BA, Gusarova NK. Mendeleev Commun. 2009; 19: 295
    • 12b Gusarova NK, Arbuzova SN, Trofimov BA. Pure Appl. Chem. 2012; 84: 439
  • 13 Clarke PA, Santos S, Martin WH. Green Chem. 2007; 9: 438
    • 14a Mayer U, Gutmann V, Gerger W. Monatsh. Chem. 1975; 106: 1235
    • 14b Malavolta L, Poletti EF, Silva EH, Schreier S, Nakaie CR. Int. J. Mol. Sci. 2008; 9: 1321
    • 15a Bader RF. W. Atoms in Molecules, A Quantum Theory 1990
    • 15b Afonin AV, Vashchenko AV, Sigalov MV. Org. Biomol. Chem. 2016; 14: 11199
  • 16 Radai Z, Kiss NZ, Czugler M, Karaghiosoff K, Keglevich G. Acta Crystallogr. Ser. C 2019; 75: 283
    • 17a Bodenhausen G, Ruben D. J. Chem. Phys. Lett. 1980; 69: 185
    • 17b Bax A, Summers MF. J. Am. Chem. Soc. 1986; 108: 2093
  • 18 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision D.01 . Gaussian, Inc; Wallingford: 2009
    • 19a Becke AD. J. Chem. Phys. 1993; 98: 5648
    • 19b Krishnan RJ, Binkley S, Seeger R, Pople JA. J. Chem. Phys. 1980; 72: 650
  • 20 Keith TA. AIMAll (Version 14.10.27) . TK Gristmill Software; Overland Park (KS, USA): 2014