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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 20
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Articles

Synthesis of phosphonates from phenylphosphonic acid and its monoesters

Réka HenyeczDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, HungaryView further author information
,
Adrienn KissDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, HungaryView further author information
,
Virág MóroczDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, HungaryView further author information
,
Nóra Zsuzsa KissDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, HungaryView further author information
&
György KeglevichDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, HungaryCorrespondence[email protected]
View further author information
Pages 2642-2650 | Received 24 May 2019, Published online: 16 Jul 2019

References

  • Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000. ISBN: 978-0-471-31824-8.
  • Kiss, N. Z.; Keglevich, G. Methods for the Preparation of Phosphinates and Phosphonates with a Focus on Recent Advances. In Organophosphorus Chemistry – Novel Developments; Keglevich, G., Ed.; De Gruyter: Berlin, 2018; pp 35–52.
  • Kiss, N. Z.; Keglevich, G. An Overview of the Synthesis of Phosphinates and Phosphinic Amides. Curr. Org. Chem. 2014, 18, 2673–2690. doi:10.2174/1385272819666140829011741.
  • Barton, D., Ollis, W. D. (Eds.). Comprehensive Organic Chemistry, Vol. 2, Sutherland, I. O. (Vol. Ed.); Pergamon: Oxford, 1979. ISBN: 978–0080213149.
  • Kosolapoff, G. M.; Maier, L. Phosphonic acids and derivatives, In Organic Phosphorus Compounds; Kosolapoff, G. M.; Maier, L., Eds.; Wiley-Interscience: New York, 1973; Vol. 6, Ch. 18, p. 1. ISBN: 978–0471504467.
  • Keglevich, G.; Kiss, N. Z.; Mucsi, Z.; Jablonkai, E.; Balint, E. The Synthesis of Phosphinates: Traditional versus Green Chemical Approaches. Green Proc. Synth. 2014, 3, 103–110. doi:10.1515/gps-2013-0106.
  • Kiss, N. Z.; Bottger, E.; Drahos, L.; Keglevich, G. Microwave-Assisted Direct Esterification of Cyclic Phosphinic Acids. Heteroatom. Chem. 2013, 24, 283–288. doi:10.1002/hc.21092.
  • Kiss, N. Z.; Keglevich, G. Microwave-Assisted Direct Esterification of Cyclic Phosphinic Acids in the Presence of Ionic Liquids. Tetrahedron Lett. 2016, 57, 971–974. doi:10.1016/j.tetlet.2016.01.044.
  • Kiss, N. Z.; Mucsi, Z.; Böttger, É.; Drahos, L.; Keglevich, G. A Three-Step Conversion of Phenyl-1H-Phosphinic Acid to Dialkyl Phenylphosphonates Including Two Microwave-Assisted Direct Esterification Steps. Curr. Org. Synthesis 2014, 11, 767–772. doi:10.2174/1570179410666131212231130.
  • Kiss, N. Z.; Keglevich, G. Direct Esterification of Phosphinic and Phosphonic Acids Enhanced by Ionic Liquid Additives. Pure Appl. Chem. 2019, 91, 59–65. doi:10.1515/pac-2018-1008.
  • Crenshaw, M. D. Synthesis of Alkyl- and Arylphosphonic Acid Monoesters by Direct Esterification of Dibasic Phosphonic Acids in the Presence of an Arsonic Acid Catalyst. Phosphorus Sulfur Silicon Relat. Elem. 2004, 179, 1509–1516. doi:10.1080/10426500490464032.
  • Szabó, A.; Jászay, Z. M.; Töke, L.; Petneházy, I. Interesting By-Products in the Synthesis of Chiral a-Aminophosphinates from Enantiopure Sulfinimines. Tetrahedron Lett. 2004, 45, 1991–1994. doi:10.1016/j.tetlet.2003.12.151.
  • Jablonkai, E.; Keglevich, G. P-Ligand-Free, Microwave-Assisted Variation of the Hirao Reaction under Solvent-Free Conditions; the P–C Coupling Reaction of > P(O)H Species and Bromoarenes. Tetrahedron Lett. 2013, 54, 4185–4188. doi:10.1016/j.tetlet.2013.05.111.
  • Chen, T.-H.; Reddy, D. M.; Lee, C.-F. A Palladium-Catalyzed Oxidative Cross-Coupling Reaction between Aryl Pinacol Boronates and H-Phosphonates in Ethanol. RSC Adv. 2017, 7, 30214–30220. doi:10.1039/C7RA04619G.
  • Iranpoor, N.; Firouzabadi, H.; Moghadam, K. R.; Motavalli, S. First Reusable Ligand-Free Palladium Catalyzed C–P Bond Formation of Aryl Halides with Trialkylphosphites in Neat Water. RSC Adv. 2014, 4, 55732–55737. doi:10.1039/C4RA07680J.

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