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An Efficient α-Phosphoryloxylation of Ketones

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DOI: 10.4236/ijoc.2011.11001    5,686 Downloads   13,344 Views   Citations
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ABSTRACT

An efficient α-phosphoryloxylation of ketones has been developed. When ketones were treated with (diace-toxyiodo)benzene and phosphates in CH2Cl2 at room temperature, the α-phosphoryloxylaction of ketones was easily be carried out, providing the ketol phosphates in good yields.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Y. Pu and J. Yan, "An Efficient α-Phosphoryloxylation of Ketones," International Journal of Organic Chemistry, Vol. 1 No. 1, 2011, pp. 1-5. doi: 10.4236/ijoc.2011.11001.

References

[1] A. Varvoglis, “Chemical Transformations Induced by Hypervalent Iodine Reagents,” Tetrahedron, Vol. 53, No. 4, 1997, pp. 1179-1255. doi:10.1016/S0040-4020(96)00970-2
[2] P. J. Stang and V. V. Zhdankin, “Organic Polyvalent Iodine Compounds,” Chemical Reviews, Vol. 96, No. 3, 1996, pp. 1123-1178. doi:10.1021/cr940424+
[3] V. V. Zhdankin and P. J. Stang, “Recent Developments in the Chemistry of Polyvalent Iodine Compounds,” Chemical Reviews, Vol. 102, No. 7, 2002, pp. 2523-2584. doi:10.1021/cr010003+
[4] T. Wirth and U. H. Hirt, “Hypervalent Iodine Compounds: Recent Advances in Synthetic Applications,” Synthesis, No. 8, 1999, pp. 1271-1287. doi:10.1055/s-1999-3540
[5] A. Kirschning, “Hypervalent Iodine and Carbohydrates - A New Liaison,” European Journal of Organic Chemistry, No. 11, 1998, pp. 2267-2274. doi:10.1002/(SICI)1099-0690(199811)1998:11<2267::AID-EJOC2267>3.0.CO;2-E
[6] M. Ochiai, “Nucleophilic Vinylic Substitutions of λ3-Vinyliodanes,” Journal of Organometallic Chemistry, Vol. 611, No. 1-2, 2000, pp. 494-508. doi:10.1016/S0022-328X(00)00487-3
[7] T. Okuyama, “Solvolysis of Vinyl Iodonium Salts. New Insights into Vinyl Cation Intermediates,” Accounts of Chemical Research, Vol. 35, No. 1, 2002, pp. 12-18. doi:10.1021/ar0100374
[8] V. V. Zhdankin and P. J. Stang, “Alkynyliodonium Salts in Organic Synthesis,” Tetrahedron, Vol. 54, No. 37, 1998, pp. 10927-10966. doi:10.1016/S0040-4020(98)00410-4
[9] V. V. Grushin, “Cyclic Diaryliodonium Ions: Old Mysteries Solved Andnew Applications Envisaged,” Chemical Society Reviews, Vol. 29, No. 5, 2000, pp. 315-324. doi:10.1039/a909041j
[10] A. C. Boye, D. Meyer, C. K. Ingison, A. N. French and T. Wirth, “Novel Lactonization with Phenonium Ion Participation Induced by Hypervalent Iodine Reagents,” Organic Letters, Vol. 5, No. 12, 2003, pp. 2157-2159. doi:10.1021/ol034616f
[11] R. M. Moriarty, R. K. Vaid and G. F. Koser, “[Hydroxy(organosulfonyloxy)iodo]arenes in Organic Synthesis,” Synlett, No. 7, 1990, pp. 365-383. doi:10.1055/s-1990-21097
[12] J. C. Lee and J. H. Choi, “Highly Efficient α-Organosulfonyloxylation of Carbonyl Compounds under Microwave Irradiation,” Synlett, No. 2, 2001, pp. 234-235.
[13] J. Akiike, Y. Yamamoto and H. Togo, “Efficient Conversion of Ketones to α-Tosyloxyketones with m-Chloroperbenzoic Acid and p-Toluenesulfonic Acid in the Presence of Catalytic Amount of IL-Supported PhI in [emim]Ots,” Synlett, No. 14, 2007, pp. 2168-2172.
[14] M. Ueno, T. Nabana and H. Togo, “Novel Oxidative α-Tosyloxylation of Alcohols with Iodosylbenzene and p-Toluenesulfonic Acid and Its Synthetic Use for Direct Preparation of Heteroaromatics,” Journal of Organic Chemistry, Vol. 68, No. 16, 2003, pp. 6424-6426. doi:10.1021/jo030045t
[15] Y. Yamamoto, Y. Kawano, P. H. Toy and H. Togo, “PhI- and Polymer-supported PhI-catalyzed Oxidative Conversion of Ketones and Alcohols to α-Tosyloxyketones with m-Chloroperbenzoic Acid and p-Toluenesulfonic Acid,” Tetrahedron, Vol. 63, No. 22, 2007, pp. 4680-4687. doi:10.1016/j.tet.2007.03.091
[16] T. Dohi and Y. Kita, “Hypervalent Iodine Reagents as A New Entrance to Organocatalysts,” Chemical Communications, No. 16, 2009, pp. 2073-2085.
[17] A. Tanaka and H. Togo, “4-MeC6H4I-Mediated Efficient α-Tosyloxylation of Ketones with Oxone? and p-Toluenesulfonic Acid in Acetonitrile,” Synlett, No. 20, 2009, pp. 3360-3364.
[18] G. F. Koser, J. S. Lodaya, D. G. Ray and P. B. Kokil, “Direct α-Phosphoryloxylation of Ketones and (Phosphoryloxy)lactonization of Pentenoic Acids with [Hydroxy[(bis(phenyloxy)phosphoryl)oxy]iodo]benzene,” Journal of the American Chemical Society, Vol. 110, No. 9, 1988, pp. 2987-2988. doi:10.1021/ja00217a058
[19] T. Nabana and H. Togo, “Reactivities of Novel [Hydroxy(tosyloxy)iodo]arenes and [Hdroxy(phophoryloxy)- iodo]arenes for α-Tosyloxylation and α-Phosphoryloxylation of Ketones,” Journal of Organic Chemistry, Vol. 67, No. 12, 2002, pp. 4362-4365. doi:10.1021/jo0200670
[20] P. J. Stang, M. Boeshar and J. Li, “Acetylenic Esters. Preparation and Characterization of Hitherto Unknown Alkynyl Carboxylate, RC.tplbond.COCOR1, and Alkynyl Phosphate, RC.tplbond.COPO(OR1)2, Esters,” Journal of the American Chemical Society, Vol. 108, No. 24, 1986, pp. 7832-7834. doi:10.1021/ja00284a057
[21] R. M. Moriarty, C. Condeiu, A. Tao and O. Prakash, “New Organohypervalent Iodine Reagents for α-Methylphosphonylations and α-Diphenyl- and α-Dimethylphosphinylations,” Tetrahedron Letters, Vol. 38, No. 14, 1997, pp. 2401-2404. doi:10.1016/S0040-4039(97)00388-2

  
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