Abstract
The reduction of acenaphthene-1-(2,6-diisopropylphenyl)imino-2-one (Dpp-Mian) by gallium in the presence of iodine primarily results in a bis(ligand) paramagnetic derivative [(Dpp-Mian)2GaI] and then to a dimeric diamagnetic complex [(Dpp-Mian)GaI]2, the reaction of which with PhC≡CH gives a cycloaddition product [{Dpp-Mian(HC=CPh)}GaI]2. The new compounds are characterized by IR spectroscopy and 1H NMR spectroscopy. The structures of complexes (Dpp-Mian)2GaI and [{Dpp- Mian(HC=CPh)}GaI]2 are determined by X-ray structure analysis (CIF files CCDC nos. 1571860 and 1571861, respectively). The catalytic activity tests for compounds [(Dpp-Mian)GaI]2 and [{Dpp-Mian(HC=CPh)}GaI]2 are conducted in the reactions of 4-chloroaniline with phenylacetylene and carbodiimide and in the reaction of phenylacetylene with 1-naphthol.
Similar content being viewed by others
References
Siebenlist, R., Frühauf, H.-W., Vrieze, K., et al., Organometallics, 2002, vol. 21, p. 5628.
Scholz, J. and Görls, H., Inorg. Chem., 1996, vol. 35, p. 4378.
Scholz, J., Görls, H., Schumann, H., and Weimann, R., Organometallics, 2001, vol. 20, p. 4394.
Fedushkin, I.L., Nikipelov, A.S., and Lyssenko, K.A., J. Am. Chem. Soc., 2010, vol. 132, p. 7874.
Fedushkin, I.L., Nikipelov, A.S., Morozov, A.G., et al., Chem.-Eur. J., 2012, vol. 18, p. 255.
Fedushkin, I.L., Moskalev, M.V., Lukoyanov, A.N., et al., Chem.-Eur. J., 2012, vol. 18, p. 11264.
Zhao, Y., Liu, Y., Lei, Y., et al., Chem. Commun., 2013, vol. 49, p. 4546.
Fedushkin, I.L., Moskalev, M.V., Baranov, E.V., and Abakumov, G.A., J. Organomet. Chem., 2013, vol. 747, p. 235.
Fedushkin, I.L., Kazarina, O.V., Lukoyanov, A.N., et al., Organometallics, 2015, vol. 34, p. 1498.
Stephan, D.W. and Erker, G., Angew. Chem., Int. Ed. Engl., 2010, vol. 49, p. 46.
Stephan, D.W., Acc. Chem. Res., 2015, vol. 48, p. 306.
Frustrated Lewis Pairs: Themed Collection, Dalton Trans., 2012, vol. 41, p. 8999
Fedushkin, I.L., Khvoinova, N.M., Skatova, A.A., and Fukin, G.K., Angew. Chem., Int. Ed. Engl., 2003, vol. 42, p. 5223.
Moskalev, M.V., Yakub, A.M., Morozov, A.G., et al., Eur. J. Org. Chem., 2015, p. 5781.
Kazarina, O.V., Moskalev, M.V., and Fedushkin, I.L., Russ. Chem. Bull. Int. Ed., 2015, vol. 1, p. 32.
Fedushkin, I.L., Morozov, A.G., Chudakova, V.A., et al., Eur. J. Inorg. Chem., 2009, p. 4995.
Yakub, A.M., Moskalev, M.V., Bazyakina, N.L., et al., Russ. Chem. Bull. Int. Ed., 2016, vol. 12, p. 2887.
Razborov, D.A., Lukoyanov, A.N., Makarov, V.M., et al., Russ. Chem. Bull. Int. Ed., 2015, vol. 10, p. 2377.
Razborov, D.A., Lukoyanov, A.N., Baranov, E.V., and Fedushkin, I.L., Dalton Trans., 2015, vol. 44, p. 20532.
SAINT. Data Reduction and Correction Program. Version 8.27B, Madison: Bruker AXS, 2012.
Sheldrick G.M., SADABS. Version 2014/2. Bruker/Siemens Area Detector Absorption Correction Program, Madison: Bruker AXS, 2014.
Sheldrick G.M., SHELXTL. Version. 6.14. Structure Determination Software Suite, Madison: Bruker AXS, 2003.
Sheldrick, G.M., Acta Crystfllogr., Sect. A: Found. Adv., 2015, vol. 71, p. 3.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © D.A. Razborov, A.N. Lukoyanov, M.V. Moskalev, E.V. Baranov, I.L. Fedyushkin, 2018, published in Koordinatsionnaya Khimiya, 2018, Vol. 44, No. 3, pp. 176–183.
Rights and permissions
About this article
Cite this article
Razborov, D.A., Lukoyanov, A.N., Moskalev, M.V. et al. Gallium Complexes with Acenaphthene-1-Imino-2-one: Synthesis and Reactivity. Russ J Coord Chem 44, 380–387 (2018). https://doi.org/10.1134/S1070328418060040
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070328418060040