Abstract
A new protocol of the synthesis of 3,3′-diaryl-3,3′-diphthalides by dehalogenation of o-keto carboxylic acid pseudochlorides is implemented. The feature of the new protocol is that the reaction is carried out in the presence of a zero-valent nickel complex catalyst generated in situ by mixing zinc powder, nickel(II) chloride, triphenylphosphine, and 2,2′-bipyridine. Along with the target dimerization products of pseudochlorides, minor products were isolated, whose structure allowed to propose possible schemes of side reactions.
Similar content being viewed by others
References
Ullman, F., Lieb. Ann., 1896, vol. 291, p. 17. doi https://doi.org/10.1002/jlac.18962910105
Meyer, H., Monatsh. Chem., 1904, vol. 25, p. 1177. doi https://doi.org/10.1007/BF01527228
Bauer, H. and Endres, G., J. Pr. Chem., 1913, vol. 87, p. 545. doi https://doi.org/10.1002/prac.19130870136
Eckert, A. and Pollack, R., Monatsh. Chem., 1917, vol. 38, p. 11. doi https://doi.org/10.1007/BF01522005
Creighton, A.R. and Jackman, L.M., J. Chem. Soc., 1960, p. 3138. doi https://doi.org/10.1039/JR9600003138
Bhatt, M.V., Kamath, K.M., and Ravindranathan, M., J. Chem. Soc. C, 1971, p. 3344 doi https://doi.org/10.1039/J39710003344
Kruppa, G., Hug, P., Liégard, A., Rist, G., and Nesvadba, P., Helv. Chim. Acta, 1993, vol. 76, p. 1821. doi https://doi.org/10.1002/hlca.19930760503
Colon, I. and Kelsey, D.R., J. Org. Chem., 1986, vol. 51, p. 2627. doi https://doi.org/10.1021/jo00364a002
Kraikin, V.A., Kuznetsov, S.I., Laktionov, V.M., and Salazkin, S.N., Polym. Sci., Ser. A, 2002, vol. 44, p. 518.
Bhatt, M.V., Kamath, K.M., and Ravindranathan, M., J. Chem. Soc. C, 1971, p. 1772 doi https://doi.org/10.1039/J39710001772
Wolfe, J.F. and Stille, J.K., Macromolecules, 1976, vol. 9, p. 489. doi https://doi.org/10.1021/ma60051a020
Groggins, P.H., Ind. Eng. Chem., 1930, vol. 22, p. 620. doi https://doi.org/10.1021/ie50246a019
Kipper, H., Ber., 1905, vol. 38, p. 2490. doi https://doi.org/10.1002/cber.19050380313
Sheldrick, G.M., Acta Cryst., 2008, vol. A64, p. 112. doi https://doi.org/10.1107/S0108767307043930
Floutz, V.W., J. Org. Chem., 1960, vol. 25, p. 643. doi https://doi.org/10.1021/jo01074a608
Acknowledgments
The elemental analyses, IR and NMR spectra were obtained and semipreparative HPLC separation was performed at the “Khimiya Center for Collective Use”, Ufa Institute of Chemistry UFRC RAS. X-ray diffraction analysis was performed at the Agidel Center for Collective Use, Institute of Petrochemistry and Catalysis UFRC RAS.
Author information
Authors and Affiliations
Corresponding author
Additional information
Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 5, pp. 773–781.
Rights and permissions
About this article
Cite this article
Yangirov, T.A., Fatykhov, A.A., Sedova, E.A. et al. Ni(0)-Catalyzed Dimerization of o-Keto Carboxylic Acid Pseudochlorides. Russ J Org Chem 55, 670–677 (2019). https://doi.org/10.1134/S1070428019050142
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428019050142