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Formation of carbon-carbon bonds between activated alkynes and diimine ligands in the aluminum complexes

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Abstract

The gallium and aluminum complexes containing the redox-active ligand (dpp-bian)Ga-Ga(dpp-bian) (1), (dpp-bian)Al-Al(dpp-bian) (2), or (dpp-bian)AlI(Et2O) (3) (dpp-bian is 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene) react with alkyl butynoates Me-C≡C-CO2R (R = Me, Et) to form C-C bonds between the dpp-bian ligand and alkyne. The reaction of complex 1 with methyl 2-butynoate and 4-chloroaniline in a molar ratio of 1: 2: 2 affords 7-(2,6-diisopropylphenyl)-10-methylacenaphtho[1,2-b]pyridin-8(7H)-one (4) containing no gallium. In the reaction of complex 2 with methyl 2-butynoate, alkyne is inserted into the skeleton of the dpp-bian ligand to form 4-(dpp-AIE)-9-(2,6-diisopropylphenyl)-8-(1,3-dpp-2MBIDP)-3,7-dimethoxy-1,5-dialuma-9-aza-2,6-dioxabicyclo[3.3.1]nonadiene-3,7 (5) (dpp-AIE is 1-[2-(2,6-diisopropylphenylimino)acenaphthen-1(2H)-ylidene]ethyl; 1,3-dpp-2MBIDP is 1,3-bis(2,6-diisopropylphenylimino)-2-methyl-2,3-dihydro-1H-phenalen-2-yl). The reactions of complex 3 with methyl and ethyl 2-butynoates afford dimeric derivatives [-OC(OR)=C(2,3-dpp-1MBIDP)Al(I)-]2 (2,3-dpp-1MBIDP is 2,3-bis(2,6-diisopropylphenylimino)-1-methyl-2,3-dihydro-1H-phenalen-2-yl; R = Me (6), Et (7)). The reaction of complex 3 with methyl 2-butynoate gives the product isomeric to compound 6: [-OC(OCH3)=C(1,3-dpp-2MBIDP)Al(I)-]2 (8), which cleaves THF resulting in complex [-OC(OCH3)=C(1,3-dpp-2MBIDP)Al(OC4H8I)-]2 (9). Complex (dpp-bian)Al(acac) (10), obtained by the reduction of dpp-bian with aluminum in the presence of Al(acac)3 in diethyl ether at ambient temperature, is inert towards acetylene, phenylacetylene, and alkyl butynoates. Compounds 4–7 and 10 were characterized using IR spectroscopy, and compounds 4, 7, and 10 were additionally characterized by 1H NMR spectroscopy. The structures of compounds 4–7, 9, and 10 were determined by X-ray diffraction analysis.

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  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhny Novgorod, Russian Federation

    I. L. Fedushkin, M. V. Moskalev, A. A. Skatova, G. K. Fukin & G. A. Abakumov

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  1. I. L. Fedushkin
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Dedicated to the Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0731–0744, March, 2013.

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Fedushkin, I.L., Moskalev, M.V., Skatova, A.A. et al. Formation of carbon-carbon bonds between activated alkynes and diimine ligands in the aluminum complexes. Russ Chem Bull 62, 731–744 (2013). https://doi.org/10.1007/s11172-013-0100-7

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