Environmentally Benign Syntheses of α-Substituted Phosphonates: Preparation of α-Amino- and α-Hydroxyphosphonates in Water, in Ionic Liquids, and under­ Solvent-Free Conditions

Tomasz K. Olszewski

doi:10.1055/s-0033-1338588

Synthesis, Table of Contents

Synthesis 2014; 46(04): 403-429
DOI: 10.1055/s-0033-1338588

review

Environmentally Benign Syntheses of α-Substituted Phosphonates: Preparation of α-Amino- and α-Hydroxyphosphonates in Water, in Ionic Liquids, and under Solvent-Free Conditions

Tomasz K. Olszewski*

Faculty of Chemistry, Wrocław University of Technology, ul. Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland Fax: +48(71)3202427 Email: tomasz.olszewski@pwr.wroc.pl

› Author Affiliations

Abstract

All articles of this category

Dedicated to Professor Bogdan Boduszek on the occasion of his 67^th birthday

Abstract

Due to the interest in α-amino- and α-hydroxyphosphonates and their derivatives, which arises from the important biological activity exhibited by those compounds, the development of efficient protocols for their preparation is of great importance. In the last 10 years however, the chemistry of α-amino and α-hydroxyphosphonates has been witness to an explosion of research activities in the field of application of environmentally benign media. This fact can be partially attributed to the development of the field of green and sustainable chemistry and especially the implementation of green solvents that has a large potential to contribute to more sustainable processes in chemical, pharmaceutical and processing industries. This review provides the reader with an in-depth overview of advances in the synthesis of α-amino- and α-hydroxyphosphonates under eco-friendy conditions compiled into sections with respect to product type and reaction medium.

1 Introduction

2 Syntheses of α-Aminophosphonates in Environmentally Friendly Media

2.1 Reactions in Water

2.2 Reactions in Ionic Liquids

2.3 Solvent-Free Protocols

2.3.1 Reactions without Any Additives

2.3.2 Reactions Promoted by Ultrasound or Microwave Irradiation

2.3.3 Catalyzed Reactions under Solvent-Free Conditions

3 Preparation of α-Hydroxyphosphonates under Environmentally Friendly Conditions

3.1 Reactions in Water

3.2 Reactions under Solvent-Free Conditions

4 Concluding Remarks

Key words

phosphorylation - Schiff bases - ionic liquids - imines - green chemistry - phosphonic acid diesters - trialkyl phosphite

Full Text

References

References
1 Savignac P, Iorga B. Modern Phosphonate Chemistry . CRC Press LLC; Boca Raton: 2003
2 Murphy PJ. Organophosphorus Reagents: A Practical Approach in Chemistry . Oxford University Press; Oxford: 2004

3a Kukhar VP, Hudson HR. Aminophosphnic and Aminophosphnic Acids . John Wiley & Sons; Chichester: 2000
3b Lejczak B, Kafarski P. Topics in Heterocyclic Chemistry: Phosphorus Heterocycles I. Vol. 20. Bansal RK. Springer; Berlin/Heidelberg: 2009: 31-63
3c Kudzin ZH, Kudzin MH, Drabowicz J, Stevens CV. Curr. Org. Chem. 2011; 15: 2015
3d Liu BJ, Cen CC, Wu MS, Kong DL. Asian J. Chem. 2011; 23: 1417
3e Naydenova ED, Todorov P, Troev KD. Amino Acids 2010; 38: 23
3f Lewkowski J. Focus on Organometallic Chemistry Research. Cato MA. Nova Science Publishers; Hauppage (NY, USA): 2005: 167
3g Troev KD. Chemistry and Application of H-Phosphonates . Elsevier; Amsterdam: 2006. Chap. 4 (Important classes of Compounds, p. 107–144) is devoted to α-aminophosphonic acids, whereas Chap. 3 (Characteristic Reactions of P-H Group, p. 59–73) is devoted to α-hydroxyalkanephosphonic esters
3h Naydenova E, Vassilev A, Popova Yu, Troev K. Heteroat. Chem. 2003; 14: 229
3i Naydenova E, Topashka-Ancheva M, Todorov P, Yordanova Ts, Troev K. Bioorg. Med. Chem. 2006; 14: 2190
3j Naydenova E, Troev K, Topashka-Ancheva M, Hägele G, Ivanov I, Kril A. Amino Acids 2007; 33: 695
3k Naydenova E, Todorov P, Topashka-Ancheva M, Momekov G, Yordanova Ts, Konstantinov S, Troev K. Eur. J. Med. Chem. 2008; 43: 1199
3l Todorov PT, Naydenova ED, Popova J, Troev KD. Heteroat. Chem. 2008; 19: 719
3m Todorov PT, Naydenova ED, Troev KD. Heteroat. Chem. 2009; 20: 87
3n Kraicheva I, Bogomilova A, Tsacheva I, Momekov G, Troev K. Eur. J. Med. Chem. 2009; 44: 3363
3o Naydenova ED, Todorov PT, Troev KD. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 1315
3p Kraicheva I, Tsacheva I, Vodenicharova E, Tashev E, Tosheva T, Kril A, Topashka-Ancheva M, Iliev I, Gerasimova Ts, Troev K. Bioorg. Med. Chem. 2012; 20: 117

4a Ordóñez M, Rojas-Cabrera H, Cativiela C. Tetrahedron 2009; 65: 17
4b Merino P, Marques-Lopez E, Herrera RP. Adv. Synth. Catal. 2008; 350: 1195
4c Ma J.-A. Chem. Soc. Rev. 2006; 35: 630
4d Odinets IL, Matveeva EV. Curr. Org. Chem. 2010; 14: 1171
4e Ordóñez M, Sayago FJ, Cativiela C. Tetrahedron 2012; 68: 6369

5 Kolodiazhnyi OI. Tetrahedron: Asymmetry 2005; 16: 3295
6 Freedman LD, Doak GO. Chem. Rev. 1957; 57: 479
7 Franz RD. AAPS Pharm. Sci. 2001; 3 (2): E10
8 Kabachnik MI, Mastrukova TA, Shipov AE, Melentyeva TA. Tetrahedron 1960; 9: 10
9 Hirschmann R, Smith III AB, Taylor CM, Benkovic PA, Taylor SD, Yager KM, Sprengler PA, Benkovic SJ. Science 1994; 265: 234
10 Bubenik M, Rej R, Nguyen-Ba N, Attardo G, Oullet F, Chan L. Bioorg. Med. Chem. Lett. 2002; 12: 1865
11 Grembecka J, Mucha A, Cierpicki T, Kafarski P. J. Med. Chem. 2003; 46: 2641
12 Snoeck R, Holy A, Dewolf-Peeters C, Van Den Oord J, De Clercq E, Andrei G. Antimicrob. Agents Chemother. 2002; 46: 3356
13 Huang J, Chen R. Heteroat. Chem. 2000; 11: 480
14 Frechette RF, Ackerman C, Beers S, Look R, Moore J. Bioorg. Med. Chem. Lett. 1997; 7: 2169

15a Combs AP. J. Med. Chem. 2010; 53: 2333
15b Van Huijsduijnen RH, Sauer WH. B, Bombrun A, Swinnen D. J. Med. Chem. 2004; 47: 4142
15c Dang Q, Kasibhatla SR, Xiao W, Liu Y, DaRe J, Taplin F, Reddy KR, Scarlato GR, Gibson T, van Poelje PD, Potter SC, Erion MD. J. Med. Chem. 2010; 53: 441

16 Maryanoff BE. J. Med. Chem. 2004; 47: 769

17a Mattes H, Carcache D, Kalkman HO, Koller M. J. Med. Chem. 2010; 53: 5367
17b Greco MN, Hawkins MJ, Powell ET, Almond JH. R, de Garavilla L, Hall J, Minor LK, Wang Y, Corcoran TW, Di Cera E, Cantwell AM, Savvides SN, Damiano BP, Maryanoff BE. J. Med. Chem. 2007; 50: 1727
17c Lassaux P, Hamel M, Gulea M, Delbruck H, Mercuri PS, Horsfall L, Dehareng D, Kupper M, Frere J.-M, Hoffmann K, Galleni M, Bebrone C. J. Med. Chem. 2010; 53: 4862

18 Kumar TS, Zhou S.-Y, Joshi BV, Balasubramanian R, Yang T, Liang BT, Jacobson KA. J. Med. Chem. 2010; 53: 2562
19 Haemers T, Wiesner J, Van Poecke S, Goeman J, Henschker D, Beck E, Jomaa H, Van Calenbergh S. Bioorg. Med. Chem. Lett. 2006; 16: 1888

20a Balzarini J, Holy A, Jindrich J, Naesens L, Snoeck R, Schols D, De Clercq E. Antimicrob. Agents Chemother. 1993; 37: 332
20b Robbins BL, Srinivas RV, Kim C, Bischofberger N, Fridland A. Antimicrob. Agents Chemother. 1998; 42: 612

21a Kafarski P, Lejczak B. Curr. Med. Chem.: Anti-Cancer Agents 2001; 1: 301
21b Ganzhorn AJ, Hoflack J, Pelton PD, Strasser F, Chanal M.-C, Piettre SR. Bioorg. Med. Chem. 1998; 6: 1865
21c Lavielle G, Hautefaye P, Schaeffer C, Boutin JA, Cudennec CA, Pierre A. J. Med. Chem. 1991; 34: 1998

22a De Clercq E. Med. Res. Rev. 2011; 31: 118
22b Hecker SJ, Erion MD. J. Med. Chem. 2008; 51: 2328

23a Van der Jeught S, Stevens CV. Chem. Rev. 2009; 109: 2672
23b Moonen K, Laureyn I, Stevens CV. Chem. Rev. 2004; 104: 6177
23c Boduszek B, Olszewski TK, Goldeman W, Grzegolec K, Blazejewska P. Tetrahedron 2012; 68: 1223
23d Boduszek B, Olszewski TK. Heteroat. Chem. 2011; 22: 617
23e Olszewski TK, Boduszek B. Synthesis 2011; 437
23f Olszewski TK, Boduszek B. Tetrahedron 2010; 66: 8661
23g Guzik M, Olszewski TK, Boduszek B. Pol. J. Chem. 2007; 81: 1879
23h Boduszek B, Olszewski T, Goldeman W, Konieczna M. Phosphorus, Sulfur Silicon Relat. Elem. 2006; 181: 787
23i Goldeman W, Olszewski TK, Boduszek B, Sawka-Dobrowolska W. Tetrahedron 2006; 62: 4506
23j Olszewski T, Boduszek B. Pol. J. Chem. 2005; 79: 553
23k Boduszek B, Olszewski T. Pol. J. Chem. 2002; 76: 1619

24a Bal W, Bertini I, Kozłowski H, Monnani R, Scozzafava A, Siatecki Z. J. Inorg. Biochem. 1990; 40: 227
24b Olszewski TK, Galezowska J, Boduszek B, Kozlowski H. Eur. J. Org. Chem. 2007; 3539; and references cited therein
24c Podstawka E, Olszewski TK, Boduszek B, Proniewicz L. J. Phys. Chem. B 2009; 113: 12013
24d Podstawka E, Kudelski A, Olszewski TK, Boduszek B. J. Phys. Chem. B 2009; 113: 10035
24e Olszewski TK, Boduszek B, Sobek S, Kozłowski H. Tetrahedron 2006; 62: 2183

25 In Green Chemistry, two entire issues have been devoted to environmentally benign solvents. Green Solvents for Synthesis: 2011, issue 6; Green Solvents – Progress in Science and Application: 2009, issue 5.

26a Kabachnik MJ, Medved T. Izv. Akad. Nauk SSSR 1953; 1126
26b Kabachnik MJ, Medved T. Izv. Akad. Nauk SSSR 1954; 1024
26c Fields EK. J. Am. Chem. Soc. 1952; 74: 1528

27 Kaboudin B, Sorbin M. Tetrahedron Lett. 2007; 48: 9015
28 Das B, Satyalakshmi G, Suneel K, Damodar K. J. Org. Chem. 2009; 74: 8400

For reviews on organic synthesis in water, see:

29a Li CJ. Chem. Rev. 2005; 105: 3095
29b Lindström UM. Chem. Rev. 2002; 102: 2751
29c Organic Synthesis in Water. Grieco P. Blackie; London: 1998
29d Li CJ, Chan TH. Organic Reactions in Aqueous Media. Wiley; New York: 1997
29e See also the thematic issue ‘Organic Reactions in Water’ in Adv. Synth. Catal. 2002, 344, 219–451
29f Organic Reactions in Water. Lindström UM. Blackwell; Oxford: 2007
29g Aqueous-Phase Organometallic Catalysis: Concept and Applications. Cornils B, Herrmann WA. Wiley-VCH; Weinheim: 2004. 2nd ed.
29h Li C.-J. Chem. Rev. 1993; 93: 2023
29i Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68
29j Shaughnessy KH, DeVasher RB. Curr. Org. Chem. 2005; 9: 585
29k Lipshutz BH, Ghorai S. Aldrichimica Acta 2008; 41: 59

30 Manabe K, Kobayashi S. Chem. Commun. 2000; 669
31 Sobhani S, Vafaee A. Synthesis 2009; 1909
32 Ando K, Egami T. Heteroat. Chem. 2011; 22: 358
33 Sundar CS, Srinivasulu D, Nayak SK, Reddy CS. Phosphorus, Sulfur Silicon Relat. Elem. 2012; 187: 523
34 Torres VM, Posa M, Srdjenovic B, Simplicio AL. Colloids Surf., B 2011; 82: 46
35 Garcia-Benjume ML, Espitia-Cabrera MI, Contreras-Garcia ME. Mater. Charact. 2009; 60: 1482

For recent comprehensive reviews on cyclodextrins, see:

36a Chen Y, Liu Y. Chem. Soc. Rev. 2010; 39: 495
36b Bellia F, La Mendola D, Pedone C, Rizzarelli E, Saviano M, Vecchio G. Chem. Soc. Rev. 2009; 38: 2756
36c Easton CJ. Pure Appl. Chem. 2005; 77: 1865
36d Szejtli J. Pure Appl. Chem. 2004; 76: 1825

37 Sobhani S, Safaei E, Asadi M, Jalili F. J. Organomet. Chem. 2008; 693: 3313

38a Akhlaghinia B, Tavakoli S, Asadi M, Safaei E. J. Porphyrins Phthalocyanines 2006; 10: 167
38b Akhlaghinia B, Asadi M, Safaei E, Heydarpoor E. Phosphorus, Sulfur Silicon Relat. Elem. 2004; 179: 2099
38c Akhlaghinia B, Asadi M, Safaei E, Heydarpoor E. J. Porphyrins Phthalocyanines 2004; 8: 1285

39 Rao KU. M, Jayaprakash SH, Nayak SK, Reddy CS. Catal. Sci. Technol. 2011; 1: 1665
40 Akiyama T, Matsuda K, Fuchibe K. Synthesis 2005; 2606

41a Clark JH. Acc. Chem. Res. 2002; 35: 791
41b Okuhara T. Chem. Rev. 2002; 102: 3641

42 Lee JC, Choi II K, Koh HY, Kang Y, Kim Y, Kang Y, Cho YS. Synthesis 2001; 81

43a Matsatsinis NF. Green Industrial Applications of Ionic Liquids. Springer; Amsterdam: 2003
43b Wasserscheid P, Welton T. Ionic Liquids in Synthesis . Wiley-VHC; Weinheim: 2003
43c Wasserscheid P, Keim W. Angew. Chem. Int. Ed. 2000; 39: 3772
43d Welton T. Chem. Rev. 1999; 99: 2071
43e Parvulescu VI, Hardacre C. Chem. Rev. 2007; 107: 2615

44 Lee S, Park JH, Kang J, Lee JK. Chem. Commun. 2001; 1698
45 Yadav JS, Reddy BV. S, Sreedhar P. Green Chem. 2002; 4: 436
46 Yadav JS, Reddy BV. S, Sreedhar P. Adv. Synth. Catal. 2003; 345: 564
47 Akbari J, Heydari A. Tetrahedron Lett. 2009; 50: 4236
48 Fang D, Jiao C, Ni C. Heteroat. Chem. 2010; 21: 546
49 Fang D, Jiao C, Ji B. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 2520
50 Fang D, Yang J, Ni C. Heteroat. Chem. 2011; 22: 5
51 Hajinasiri R, Hossaini Z, Rosrami-Charati F. Heteroat. Chem. 2011; 22: 625
52 Jin L, Song B, Zhang G, Xu R, Zhang S, Gao X, Hu D, Yang S. Bioorg. Med. Chem. Lett. 2006; 16: 1537
53 Reddy MV, Dindulkar SD, Jeong YT. Tetrahedron Lett. 2011; 52: 4764
54 Dake SA, Raut DS, Kharat KR, Mhaske RS, Deshmukh SU, Pawar RP. Bioorg. Med. Chem. Lett. 2011; 21: 2527
55 Disale ST, Kale SR, Kahandal SS, Srinivasan TG, Jayaram RV. Tetrahedron Lett. 2012; 53: 2277
56 Ranu BC, Hajra A. Green Chem. 2002; 4: 551
57 Hetzer RH, Gais H.-J, Raabe G. Synthesis 2008; 1126

For recent reviews of microwave use, see:

58a Kappe CO, Pieber B, Dallinger D. Angew. Chem. Int. Ed. 2013; 52: 1088
58b Kappe CO. Acc. Chem. Res. 2013; 46: 1579

For recent reviews of application of ultrasound, see:

58c Cravotto G, Cintas P. Chem. Soc. Rev. 2006; 35: 180
58d Cravotto G, Cintas P. Chem. Eur. J. 2007; 13: 1902

59 Yadav JS, Reddy BV. S, Madan Ch. Synlett 2001; 1131
60 Kabachnik MM, Zobnina EV, Beletskaya IP. Synlett 2005; 1393
61 Xia M, Lu Y. Ultrason. Sonochem. 2007; 14: 235
62 Dar B, Singh A, Sahu A, Patidar P, Chakraborty A, Sharma M, Singh B. Tetrahedron Lett. 2012; 53: 5497
63 Firouzabadi H, Iranpoor N, Sobhani S. Synthesis 2004; 2692
64 Bhagat S, Chakraborti AK. J. Org. Chem. 2007; 72: 1263
65 Bhagat S, Chakraborti AK. J. Org. Chem. 2008; 73: 6029
66 Hou J.-T, Gao J.-W, Zhang Z.-H. Appl. Organomet. Chem. 2011; 25: 47
67 Tibhe GD, Bedolla-Medrono M, Cativiela C, Ordóñez M. Synlett 2012; 23: 1931
68 Sharghi H, Ebrahimpourmoghaddam S, Doroodmand MM. Tetrahedron 2013; 69: 4708
69 Pokalwar RU, Sadaphal SA, Kategaonkar AH, Shingate BB, Shingare MS. Green Chem. Lett. Rev. 2010; 3: 33
70 Heydari A, Arefi A, Khaksar S, Tajbakhsh M. Catal. Commun. 2006; 7: 982
71 Jahani F, Zamenian B, Khaksar S, Tajbakhsh M. Synthesis 2010; 3315
72 Shankar J, Karnakar K, Srinivas B, Nageswar YV. D. Tetrahedron Lett. 2010; 51: 3938
73 Sonar SS, Kategaonkar AH, Ware MN, Gill CH, Shingate BB, Shingare MS. ARKIVOC 2009; (ii): 138
74 de Noronha RG, Costa PJ, Romão CC, Calhorda MJ, Fernandes AC. Organometallics 2009; 28: 6206
75 Mandhane PG, Joshi RS, Nagargoje DR, Gill CH. Tetrahedron Lett. 2010; 51: 1490

For reviews on aplications of Nafion^®, see:

76a Seen AJ. J. Mol. Catal. A: Chem. 2001; 177: 105
76b Mauritz KA, Moore RB. Chem. Rev. 2004; 104: 4535

77 Weng SS, Lin GY, Li H.-C, Yang K.-C, Yang TM, Liu H.-C, Sie S.-H. Appl. Organomet. Chem. 2012; 26: 455
78 Zhou X, Liu Y, Chang L, Zhao J, Shang D, Liu X, Lin L, Feng X. Adv. Synth. Catal. 2009; 351: 2567

79a Samanta S, Zhao CG. J. Am. Chem. Soc. 2006; 128: 7442
79b Mandal T, Samanta S, Zhao CG. Org. Lett. 2007; 9: 943
79c Liu J, Yang Z, Wang Z, Wang F, Chen X, Liu X, Feng X, Su Z, Hu C. J. Am. Chem. Soc. 2008; 130: 5654
79d Chen X, Wang J, Zhu Y, Shang Y, Gao B, Liu X, Feng X, Su Z, Hu C. Chem. Eur. J. 2008; 14: 10896

80 Zhou S, Wu Z, Rong J, Wang S, Yang G, Zhu X, Zhang L. Chem. Eur. J. 2012; 18: 2653

For general reviews and books on application of microreactions and flow-chemistry, see:

81a Protasova LN, Bulut M, Ormerod D, Buekenhoudt A, Berton J, Stevens CV. Org. Process Res. Dev. 2013; 17: 760
81b Mason BP, Price KE, Steinbacher JL, Bogdan AR, McQuade DT. Chem. Rev. 2007; 107: 2300
81c Wiles C, Watts P. Micro Reaction Technology in Organic Synthesis. CRC Press Taylor & Francis Group; Boca Raton: 2011
81d Hessel V, Renken A, Schouten JC, Yoshida J. Micro Process Engineering: A Comprehensive Handbook. Wiley-VCH; Weinheim: 2009
81e Jahnisch K, Hessel V, Lowe H, Baerns M. Angew. Chem. Int. Ed. 2004; 43: 406

82 An isolated example of the synthesis of (α-aminophospho-nates under microreactor conditions, albeit with the use of classical solvents: Van Meenen E, Moonen K, Acke D, Stevens CV. ARKIVOC 2006; (i): 31

Environmentally Benign Syntheses of α-Substituted Phosphonates: Preparation of α-Amino- and α-Hydroxyphosphonates in Water, in Ionic Liquids, and under­ Solvent-Free Conditions

Environmentally Benign Syntheses of α-Substituted Phosphonates: Preparation of α-Amino- and α-Hydroxyphosphonates in Water, in Ionic Liquids, and under Solvent-Free Conditions