Tính tan của Axit Phenylboronic và các Este Vòng của nó trong Các Dung Môi Hữu Cơ

Hall, D.G. (ed.): Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. Wiley, Weinheim (2011) Nishiyabu, R., Kubo, Y., James, T.D., Fossey, J.S.: Boronic acid building blocks: tools for sensing and separation. Chem. Commun. 47, 1106–1123 (2011). https://doi.org/10.1039/c0cc02920c Adamczyk-Woźniak, A., Borys, K.M., Sporzyński, A.: Recent developments in the chemistry and biological applications of benzoxaboroles. Chem. Rev. 115, 5224–5247 (2015). https://doi.org/10.1021/cr500642d Adamczyk-Woźniak, A., Sporzyński, A.: Diboronic acids and their derivatives: new perspectives in sensing and materials’ chemistry. In: Wythers, M.C. (ed.) Advances in Materials Science Research, pp. 201–233. Nova Science Publishers Inc., Hauppauge (2018) Suzuki, A.: Cross-coupling reactions of organoboranes: an easy way to construct C-C bonds (Nobel Lecture). Angew. Chem. Int. Ed. 50, 6723–6737 (2011). https://doi.org/10.1002/anie.201101379 Whyte, G.F., Vilar, R., Woscholski, R.: Molecular recognition with boronic acids—applications in chemical biology. J. Chem. Biol. 6, 161–174 (2013). https://doi.org/10.1007/s12154-013-0099-0 Ding, S.Y., Wang, W.: Covalent organic frameworks (COFs): from design to applications. Chem. Soc. Rev. 42, 548–568 (2013). https://doi.org/10.1039/c2cs35072f António, J.P.M., Russo, R., Carvalho, C.P., Cal, P.M.S.D., Gois, P.M.P.: Boronic acids as building blocks for the construction of therapeutically useful bioconjugates. Chem. Soc. Rev. 48, 3513–3536 (2019). https://doi.org/10.1039/c9cs00184k Washburn, R.M., Levens, E., Albright, C.F., Billig, F.A.: Benzeneboronic Anhydride. Organic Syntheses (Collected Volume) 4, 68 (1963). https://doi.org/10.15227/orgsyn.039.0003 Khan, R.I., Pitchumani, K.: A pyridinium modified β-cyclodextrin: an ionic supramolecular ligand for palladium acetate in c–c coupling reactions in water. Green Chem. 18, 5518–5528 (2016). https://doi.org/10.1039/c6gc01326k Firouzabadi, H., Iranpoor, N., Ghaderi, A., Gholinejad, M., Rahimi, S., Jokar, S.: Design and synthesis of a new phosphinite—functionalized clay composite for the stabilization of palladium nanoparticles. Application as a recoverable catalyst for C–C bond formation reactions. RSC Adv. 4, 27674–27682 (2014). https://doi.org/10.1039/c4ra03645j Leszczyński, P., Sporzyński, A.: Solubility of phenylboronic compounds in water. Mediter. J. Chem. 6, 200–207 (2017). https://doi.org/10.13171/mjc65/01711030630-sporzynski Lopalco, A., Marinaro, W.A., Day, V.W., Stella, V.J.: Isolation, solubility, and characterization of d-mannitol esters of 4-methoxybenzeneboronic acid. J. Pharm. Sci. 106, 601–610 (2017). https://doi.org/10.1016/j.xphs.2016.10.022 Cao, Z., Nandhikonda, P., Heagy, M.D.: Highly water-soluble monoboronic acid probes that show optical sensitivity to glucose based on 4-sulfo-1,8-naphthalic anhydride. J. Org. Chem. 74, 3544–3546 (2009). https://doi.org/10.1021/jo9002008 Fang, G., Bian, Z., Liu, D., Wu, G., Wang, H., Wu, Z., Yao, Q.: Water—soluble diboronic acid—based fluorescent sensors recognizing D-sorbitol. New J. Chem. 43, 13802–13809 (2019). https://doi.org/10.1039/c9nj02636c Lennox, A.J.J., Lloyd-Jones, G.C.: Selection of boron reagents for Suzuki-Miyaura coupling. Chem. Soc. Rev. 43, 412–443 (2014). https://doi.org/10.1039/c3cs60197h Ashworth, I.W., Campbell, A.D., Cherryman, J.H., Clark, J., Crampton, A., Eden-Rump, E.G.B., Evans, M., Jones, M.F., McKeever-Abbas, S., Meadows, R.E., Skilling, K., Whittaker, D.T.E., Woodward, R.L., Inglesby, P.A.: Process development of a Suzuki reaction used in the manufacture of lanabecestat. Org. Process Res. Dev. 22, 1801–1808 (2018). https://doi.org/10.1021/acs.oprd.8b00312 Matuszewska, A., Uchman, M., Adamczyk-Woźniak, A., Sporzyński, A., Pispas, S., Kovacik, L., Stepanek, M.: Glucose—responsive hybrid nanoassemblies in aqueous solutions: ordered phenylboronic acid within intermixed poly-(4-hydroxystyrene)-block-poly(ethylene oxide) block copolymer. Biomacromol. 16, 3731–3739 (2015). https://doi.org/10.1021/acs.biomac.5b01325 Adamczyk-Woźniak, A., Kaczorowska, E., Kredatusova, J., Madura, I., Marek, P.H., Matuszewska, A., Sporzyński, A., Uchman, M.: Dehydration of ortho-, meta- and para-alkoxy phenylboronic acids to their corresponding boroxines. Eur. J. Inorg. Chem. (2018). https://doi.org/10.1002/ejic.201701485 Durka, K., Kurach, P., Luliński, S., Serwatowski, J.: Functionalization of dihalophenylboronic acids by deprotonation of their N-butyldiethanolamine esters. Eur. J. Org. Chem. (2009). https://doi.org/10.1002/ejoc.200900526 Hofman, T., Reda, M., Gliński, M.: Liquid–liquid equilibrium in binary systems of isomeric C8 aliphatic monoethers with nitromethane. Fluid Phase Equilib. 356, 271–276 (2013). https://doi.org/10.1016/j.fluid.2013.07.002 Redlich, O., Kister, A.T.: Algebraic representation of thermodynamic properties and the classification of solutions. Ind. Eng. Chem. 40, 345–348 (1948). https://doi.org/10.1021/ie50458a036 Wilson, G.M.: Vapor-liquid equilibrium. XI. A new expression for the excess free energy of mixing. J. Am. Chem. Soc. 86, 127–130 (1964). https://doi.org/10.1021/ja01056a002 Renon, H., Prausnitz, J.M.: Local compositions in thermodynamic excess functions for liquid mixtures. AIChEJ 14, 135–144 (1968). https://doi.org/10.1002/aic.690140124 Riddick, J.A., Bunger, W., Sakano, T.K.: Organic Solvents. Physical Properties and Methods of Purification, 4th edn. Wiley, New York (1986)