A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones
Mattia Forchetta, Valeria Conte, Giulia Fiorani, Pierluca Galloni, Federica Sabuzi
Organics · pp. 107–117 · Published 3 Jun 2021
10.3390/org2020010Abstract
Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications.
References (62)
- 1 Lyagin, I., and Efremenko, E. (2021). Enzymes, Reacting with Organophosphorus Compounds as Detoxifiers: Diversity and Functions. Int. J. Mol. Sci., 22. [DOI]
- 2 Wiemer, 2015, Prodrugs of phosphonates and phosphates: Crossing the membrane barrier [DOI]
- 3 Tan, 2004, Inhibition of SARS coronavirus infection in vitro with clinically approved antiviral drugs [DOI]
- 4 2003, Clinical Potential of the Acyclic Nucleoside Phosphonates Cidofovir, Adefovir, and Tenofovir in Treatment of DNA Virus and Retrovirus Infections [DOI]
- 5 Bray, W. (2020). Covid-19 Drug Design via Quantum Mechanical Principles Leads to a New Corona-SARS Anti- Viral Candidate 2-Phosphono-Benzoic-Acid. J. Theor. Comput. Sci.
- 6 Verbrugghen, 2013, Alpha-Heteroatom Derivatized Analogues of 3-(Acetylhydroxyamino)propyl Phosphonic Acid (FR900098) as Antimalarials [DOI]
- 7 Falagas, 2016, Fosfomycin [DOI]
- 8 Savjani, K.T., Gajjar, A.K., and Savjani, J.K. (2012). Drug solubility: Importance and enhancement techniques. ISRN Pharm., 1–10. [DOI]
- 9 Deng, 2020, Conductive Metal–Organic Frameworks: Mechanisms, Design Strategies and Recent Advances [DOI]
- 10 Hix, 2007, A Supramolecular Ladderlike Structure Formed by the Auto-Assembly of Benzene-1,3,5-triphosphonic Acid [DOI]
- 11 Montouillout, 2004, Assembly of benzene-1,3,5-tris(methylenephosphonic acid) and guanidinium salt: Single crystal-X-ray characterisation and 31P solid state NMR investigations [DOI]
- 12 Kaltbeitzel, 2011, Organic Proton-Conducting Molecules as Solid-State Separator Materials for Fuel Cell Applications [DOI]
- 13 Hotchkiss, 2012, The Modification of Indium Tin Oxide with Phosphonic Acids: Mechanism of Binding, Tuning of Surface Properties, and Potential for Use in Organic Electronic Applications [DOI]
- 14 Petit, 2012, Surface Modification Using Phosphonic Acids and Esters [DOI]
- 15 Pujari, 2014, Covalent Surface Modification of Oxide Surfaces [DOI]
- 16 Boissezon, 2014, Organophosphonates as anchoring agents onto metal oxide-based materials: Synthesis and applications [DOI]
- 17 Villemin, D., Moreau, B., Siméon, F., Maheut, G., Fernandez, C., Montouillout, V., Caignaert, V., and Jaffrès, P.A. (2001). A one step process for grafting organic pendants on alumina via the reaction of alumina and phosphonate under microwave irradiation. Chem. Commun., 2060–2061. [DOI]
- 18 Zeininger, 2016, Quantitative Determination and Comparison of the Surface Binding of Phosphonic Acid, Carboxylic Acid, and Catechol Ligands on TiO2 Nanoparticles [DOI]
- 19 Lafond, 2003, 17O MAS NMR Study of the Bonding Mode of Phosphonate Coupling Molecules in a Titanium Oxo-Alkoxo-Phosphonate and in Titania-Based Hybrid Materials [DOI]
- 20 Holland, 2007, NMR Characterization of Phosphonic Acid Capped SnO2 Nanoparticles [DOI]
- 21 Tudisco, 2012, Cyclodextrin Anchoring on Magnetic Fe3O4 Nanoparticles Modified with Phosphonic Linkers [DOI]
- 22 Zhang, 2015, Anchoring Groups for Dye-Sensitized Solar Cells [DOI]
- 23 Brauchli, 2016, Combining phosphonic acid-functionalized anchoring ligands with asymmetric ancillary ligands in bis(diimine)copper(I) dyes for dye sensitized solar cells [DOI]
- 24 Romero, 2018, Light-driven water oxidation using hybrid photosensitizer-decorated Co3O4 nanoparticles [DOI]
- 25 Xie, 2017, 9-Amino(9-deoxy)epi-cinchona alkaloid-tethered aluminium phosphonate architectures for heterogeneous cooperative catalysis: Asymmetric aldol and double-Michael cascade reaction
- 26 Angeloni, 2014, Synthesis of Zirconium Phosphonate Supported L-Proline as an Effective Organocatalyst for Direct Asymmetric Aldol Addition [DOI]
- 27 Wan, 2014, Facile one-pot fabrication of magnetic nanoparticles (MNPs)-supported organocatalysts using phosphonate as an anchor point through direct co-precipitation method [DOI]
- 28 Sabuzi, 2016, KuQuinones: A new class of quinoid compounds as photoactive species on ITO [DOI]
- 29 Bonomo, 2017, KuQuinones as sensitizers of NiO based p-type dye sensitized solar cells [DOI]
- 30 Volpato, 2020, Photoanodes for water oxidation with visible light based on a pentacyclic quinoid organic dye enabling proton-coupled electron transfer [DOI]
- 31 Valentini, 2021, Unveiling KuQuinone redox species: An electrochemical and computational cross study [DOI]
- 32 Coletti, 2012, Unexpected One-Pot Synthesis of Highly Conjugated Pentacyclic Diquinoid Compounds [DOI]
- 33 Sabuzi, 2017, KuQuinones Equilibria Assessment for Biomedical Applications [DOI]
- 34 Guerrero, 2013, Phosphonate Coupling Molecules for the Control of Surface/Interface Properties and the Synthesis of Nanomaterials [DOI]
- 35 Hagfeldt, 2010, Dye-Sensitized Solar Cells [DOI]
- 36 Gardner, 1995, Systems for Orthogonal Self-Assembly of Electroactive Monolayers on Au and ITO: An Approach to Molecular Electronics [DOI]
- 37 Lalatonne, Y., Paris, C., Serfaty, J.M., Weinmann, P., Lecouvey, M., and Motte, L. (2008). Bis-Phosphonates-Ultra Small Superparamagnetic Iron Oxide Nanoparticles: A Platform Towards Diagnosis and Therapy. Chem. Commun., 2553–2555. [DOI]
- 38 Péchy, P., Rotzinger, F.P., Nazeeruddin, M.K., Kohle, O., Zakeeruddin, S.M., Humphry-Baker, R., and Grätzel, M. (1995). Preparation of Phosphonated Polypyridyl Ligands to Anchor Transition-Metal Complexes on Oxide Surfaces: Application for the Conversion of Light to Electricity with Nanocrystalline TiO2 Films. J. Chem. Soc. Chem. Commun., 65–66. [DOI]
- 39 Koh, 2006, Phenylphosphonic Acid Functionalization of Indium Tin Oxide: Surface Chemistry and Work functions [DOI]
- 40 Michaelis, 1898, Ueber das Verhalten der Jodalkyle gegen die sogen. Phosphorigsäureester oder O-Phosphine [DOI]
- 41 Bhattacharya, 1981, The Michaelis-Arbuzov Rearrangement [DOI]
- 42 Catel, 2008, Synthesis, Photopolymerization and Adhesive Properties of New Hydrolytically Stable Phosphonic Acids for Dental Applications [DOI]
- 43 Ohashi, 1989, Syntheses of D-erythro-1-deoxydihydroceramide-1-sulfonic acid and phosphonosphingoglycolipid found in marine organisms via a common precursor [DOI]
- 44 Ragulin, 2012, ω-Haloalkylphosphoryl Compounds: Synthesis and Properties [DOI]
- 45 Hewitt, 1977, Organophosphorus compounds. P-arylated perhydro-1,2-azaphosphorines [DOI]
- 46 Matoba, 1984, Structural modification of bioactive compounds. Syntheses of aminophosphonic acids [DOI]
- 47 Groenewold, 2013, Rapid analysis of organophosphonate compounds recovered from vinyl floor tile using vacuum extraction coupled with a fast-duty cycle GC/MS [DOI]
- 48 McLafferty, 1959, Mass spectrometric analysis. Molecular rearrangements [DOI]
- 49 Li, 2010, Photopolymerization of Self-Assembled Monolayers of Diacetylenic Alkylphosphonic Acids on Group-III Nitride Substrates [DOI]
- 50 Subedi, 2018, Synthesis and biological activity investigation of azole and quinone hybridized phosphonates [DOI]
- 51 Villemin, 1998, Rapid and efficient arbuzov reaction under microwave irradiation [DOI]
- 52 Cherevatskaya, 2012, Visible-Light-Promoted Stereoselective Alkylation by Combining Heterogeneous Photocatalysis with Organocatalysis [DOI]
- 53 Sevrain, 2017, Phosphonic acid: Preparation and applications [DOI]
- 54 Ikenberry, 2014, Acid monolayer functionalized iron oxide nanoparticles as catalysts for carbohydrate hydrolysis [DOI]
- 55 Jansa, 2012, Microwave-assisted hydrolysis of phosphonate diesters: An efficient protocol for the preparation of phosphonic acids [DOI]
- 56 Besse, 2013, Synthesis and polymerization kinetics of acrylamide phosphonic acids and esters as new dentine adhesives [DOI]
- 57 Norris, 2013, Synthesis of Phosphonic Acid Derivatized Bipyridine Ligands and Their Ruthenium Complexes [DOI]
- 58 Zhou, 2018, Examining the Role of Acceptor Molecule Structure in Self-Assembled Bilayers: Surface Loading, Stability, Energy Transfer, and Upconverted Emission [DOI]
- 59 Morita, 1978, A convenient dealkylation of dialkyl phosphonates by chlorotrimethylsilane in the presence of sodium iodide [DOI]
- 60 Franz, 2001, Comparisons of pKa and log P values of some carboxylic and phosphonic acids: Synthesis and measurement [DOI]
- 61 Papadimitriou, 2010, Phosphonated fully aromatic polyethers for PEMFCs applications [DOI]
- 62 Kahraman, 2019, Synthesis and Characterization of Phosphorus- and Carborane-Containing Polyoxanorbornene Block Copolymers [DOI]
Cited by 12
Mattia Forchetta, Federica Sabuzi, Lorenzo Stella · The Journal of Organic Chemistry · 2022
Stavroula Kostoudi, Georgios Pampalakis · International Journal of Molecular Sciences · 2022
Giulia Alice Volpato, Elena Colusso, Lorenzo Paoloni · Photochemical & Photobiological Sciences · 2021
Vincenzo Mazzaracchio, Roberta Marrone, Mattia Forchetta · Electrochimica Acta · 2022
Ruggero Bonetto, Nuria Romero, Federica Sabuzi · Green Chemistry · 2025
Francesca Valentini, Federica Sabuzi, Mattia Forchetta · RSC Advances · 2023
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