Pyridine 2,6-Dicarboxylic Acid
as a Bifunctional Organocatalyst for Hydrophosphonylation
of Aldehydes and Ketones in Water

Fatemeh Jahani; Behi Zamenian; Samad Khaksar; Mahmood Tajbakhsh

doi:10.1055/s-0030-1257866

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Synthesis 2010(19): 3315-3318
DOI: 10.1055/s-0030-1257866

PAPER

Pyridine 2,6-Dicarboxylic Acid as a Bifunctional Organocatalyst for Hydrophosphonylation of Aldehydes and Ketones in Water

Fatemeh Jahani^a, Behi Zamenian^a, Samad Khaksar^b, Mahmood Tajbakhsh*^a
^a Department of Chemistry, University of Mazandaran, P.O. Box 453, Babolsar, Iran
^b Chemistry Department, Islamic Azad University, Ayatollah Amoli Branch, P.O. Box 678, Amol, Iran
Fax: +98(112)5342350; e-Mail: tajbaksh@umz.ac.ir;

Further Information

Publication History

Received 10 May 2010
Publication Date:
22 July 2010 (online)

Abstract
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Abstract

A novel organocatalytic, direct synthesis of α-hydroxy phosphonates via reaction of aldehydes and ketones with trimethylphosphite in the presence of catalytic amounts of pyridine 2,6-dicarboxylic acid in water is reported. The method is simple, cost-effective and environmentally benign.

Key words

α-hydroxy phosphonates - organocatalyst - pyridine 2,6-dicarboxylic acid - nucleophilic addition - water

References

For reviews see:
1a Dalko PI. Moisan L. Angew. Chem. Int. Ed. 2001, 40: 3726

Google Scholar
1b List B. Tetrahedron 2002, 58: 5573

Google Scholar
1c Duthaler RO. Angew. Chem. Int. Ed. 2003, 42: 975

Google Scholar
1d Dalko PI. Moisan L. Angew. Chem. Int. Ed. 2004, 116: 5248

Google Scholar
1e List B. Chem. Commun. 2006, 819

Google Scholar
1f Marigo M. Jørgensen KA. Chem. Commun. 2006, 2001

Google Scholar
1g Enders D. Grondal C. Hüttl MRM. Angew. Chem. Int. Ed. 2007, 46: 1570

Google Scholar
1h Dondoni A. Massi A. Angew. Chem. Int. Ed. 2008, 47: 4638

Google Scholar
1i Schreiner PR. Chem. Soc. Rev. 2003, 32: 289

Google Scholar
1j Doyle AG. Jacobsen EN. Chem. Rev. 2007, 107: 5713

Google Scholar
2a Csihony S. Beaudette TT. Sentman CA. Nyce WG. Waymouth MR. Hedrickb LJ. Adv. Synth. Catal. 2004, 346: 1081

Google Scholar
2b Barbas CF. Angew. Chem. Int. Ed. 2008, 47: 42

Google Scholar
2c List B. Lerner RA. Barbas CF.
J. Am. Chem. Soc. 2000, 122: 2395

Google Scholar
2d Bengoa EG. Linden A. López R. Mendiola IM. Oiarbide M. Palomo C. J. Am. Chem. Soc. 2008, 130: 7955

Google Scholar
2e Wittkopp A. Schreiner PR. Eur. J. Org. Chem. 2003, 407

Google Scholar
2f Palomo C. Oiarbide M. Mielgo A. Angew. Chem. Int. Ed. 2004, 43: 5442

Google Scholar
2g Ibrahem I. Rios R. Vesely J. Hammar P. Eriksson L. Himo F. Córdova A. Angew. Chem. Int. Ed. 2007, 46: 4507

Google Scholar
2h Carlone A. Bartoli G. Bosco M. Sambri L. Melchiorre P. Angew. Chem. Int. Ed. 2007, 46: 4504

Google Scholar
2i Maerten E. Carbrera S. Kjaersgaard A. Jørgensen KA. J. Org. Chem. 2007, 72: 8893

Google Scholar
3 Xu DQ. Wang LP. Luo SP. Wang YF. Zhang S. Xu ZY. Eur. J. Org. Chem. 2008, 1049

Crossref Google Scholar
4a Mosse S. Alexakis A. Org. Lett. 2006, 8: 3577

Google Scholar
4b McCooey SH. Connon SJ. Org. Lett. 2007, 9: 599

Google Scholar
4c Zhao JF. He L. Jiang J. Tang Z. Cun LF. Gong LZ. Tetrahedron Lett. 2008, 49: 3372

Google Scholar
5 Li CJ. Chem. Rev. 2005, 105: 3095

Crossref PubMed Google Scholar
6 Lindstrom UM. Andersson F. Angew. Chem. Int. Ed. 2006, 45: 548

Crossref Google Scholar
7 Hailes HC. Org. Process Res. Dev. 2007, 11: 114

Crossref Google Scholar
8 Patel DV. Rielly-Gauvin K. Ryono DE. Tetrahedron Lett. 1990, 31: 5591

Crossref Google Scholar
9 Patel DV. Rielly-Gauvin K. Ryono DE. Tetrahedron Lett. 1990, 31: 5587

Crossref Google Scholar
10a Stowasser B. Budt KH. Jian-Qi L. Peyman A. Ruppert D. Tetrahedron Lett. 1992, 33: 6625

Google Scholar
10b Szymanska A. Szymczak M. Boryski J. Stawinski J. Kraszewski A. Collu G. Sanna G. Giliberti G. Loddo R. La Colla P. Bioorg. Med. Chem. 2006, 14: 1924

Google Scholar
11a Snoeck R. Holy A. Dewolf-Peeters C. Van Den Oord J. De Clercq E. Andrei G. Antimicrob. Agents Chemother. 2002, 46: 3356

Google Scholar
11b Hammerschmidt F. Angew. Chem., Int. Ed. Engl. 1994, 33: 341

Google Scholar
11c Jennings LJ. Macchia M. Parkin A. J. Chem. Soc., Perkin Trans. 1992, 1: 2197

Google Scholar
11d Sikorski JA. Miller MJ. Braccoli DS. Cleary DJ. Corey SD. Font KJ. Gruys KJ. Han CY. Lin K.-C. Pansegrau PD. Ream JE. Shnur D. Shah A. Walker MC. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76: 115

Google Scholar
12 Peters ML. Leonard M. Licata AA. Cleveland Clinic J. Med. 2001, 68: 945

Crossref Google Scholar
13 Kaboudin B. Tetrahedron Lett. 2003, 44: 1051

Crossref Google Scholar
14 Nesterov VV. Kolodiazhnyi OI. Tetrahedron 2007, 63: 6720

Crossref Google Scholar
15 Eymery F. Lorga B. Savignac P. Tetrahedron 1999, 55: 2671

Crossref Google Scholar
16 Firouzabadi H. Iranpoor N. Sobhani S. Amoozgar Z. Synthesis 2004, 1771

Article in Thieme Connect Google Scholar
17 Evans DA. Hurst KM. Takacs JM. J. Am. Chem. Soc. 1978, 100: 3467

Crossref Google Scholar
18 Nakanishi K. Kotani S. Sugiura M. Nakajima M. Tetrahedron 2008, 64: 6415

Crossref Google Scholar
19 Texier-Boullet F. Foucaud A. Synthesis 1982, 916

Article in Thieme Connect Google Scholar
20 Texier-Boullet F. Lequitte M. Tetrahedron Lett. 1986, 27: 3515

Crossref Google Scholar
21 Arai T. Bougauchi M. Sasai H. Shibasaki M. J. Org. Chem. 1996, 61: 2926

Crossref Google Scholar
22 Gou S. Zhou X. Wang J. Liu X. Feng X. Tetrahedron 2008, 64: 2864

Crossref Google Scholar
23 Azizi N. Saidi MR. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178: 1255

Crossref Google Scholar
24 Heydari A. Arefi A. Khaksar S. Tajbakhsh M. Catal. Commun. 2006, 7: 982

Crossref Google Scholar
25 Alexander CW. Albiniak PA. Gibson LR. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 167: 205

Crossref Google Scholar
26 Rowe BJ. Spilling CD. Tetrahedron: Asymmetry 2001, 12: 1701

Crossref Google Scholar
27 Saito B. Egami H. Katsuki T. J. Am. Chem. Soc. 2007, 129: 1978

Crossref Google Scholar
28 Samanta S. Zhao CG. J. Am. Chem. Soc. 2006, 128: 7442

Crossref PubMed Google Scholar
29 Dodda R. Zhao CG. Org. Lett. 2006, 8: 4911

Crossref Google Scholar
30 Goldeman W. Soroka M. Synthesis 2006, 3019

Article in Thieme Connect Google Scholar
31 Vahdat M. Baharfar R. Tajbakhsh M. Heydari A. Baghbanian M. Khaksar S. Tetrahedron Lett. 2008, 49: 6501

Crossref Google Scholar
32a Kharasch MS. Mosher RA. Bengelsdorf IS.
J. Org. Chem. 1960, 25: 1000

Google Scholar
32b Sekine M. Nakajima M. Kume A. Hashizume A. Hata T. Bull. Chem. Soc. Jpn. 1982, 55: 224

Google Scholar
32c Oehler E. El-Badawi M. Zbiral E. Chem. Ber. 1985, 118: 4099

Google Scholar
32d Gancarz R. Gancarz I. Walkowiak U. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 104: 45

Google Scholar
32e Maeda H. Takahashi K. Ohmori H. Tetrahedron 1998, 54: 12233

Google Scholar
33a Timmler H. Kurz J. Chem. Ber. 1971, 104: 3740

Google Scholar
33b Hammerschmidt F. Schneyder E. Zbiral E. Chem. Ber. 1980, 113: 3891

Google Scholar
33c Arbuzov BA. Fuzhenkova AV. Banderova NA. Zh. Obshch. Khim. 1986, 56: 1691

Google Scholar
33d Hammerschmidt F. Monatsh. Chem. 1993, 124: 1063

Google Scholar
33e El Kaïm L. Gaultier L. Grimaud L. Dos Santos A. Synlett 2005, 2335

Google Scholar
34a Demir AS. Reis O. Igdir AC. Esiringue I. Eymur S. J. Org. Chem. 2005, 70: 10584

Google Scholar
34b Demir AS. Eymur S. J. Org. Chem. 2007, 72: 8527

Google Scholar
34c Demir AS. Esiringu I. Gollu M. Reis O. J. Org. Chem. 2009, 74: 2197

Google Scholar
35 Zhou X. Liu Y. Chang L. Zhao J. Shang D. Liu X. Lin L. Feng X. Adv. Synth. Catal. 2009, 16: 2567

Google Scholar
36 Prakash GKS. Panja C. Do C. Mathew T. Olah GA. Synlett 2007, 2395

Article in Thieme Connect Google Scholar
37 Tajbakhsh M. Heydari A. Khalilzadeh MA. Lakouraj MM. Zamenian B. Khaksar S. Synlett 2007, 2347

Article in Thieme Connect Google Scholar
38 Zhou W. Xu LW. Yang L. Zhao PQ. Xia CG.
J. Mol. Catal. A: Chem. 2006, 249: 129

Crossref Google Scholar