NDLI: Addition of Alkynes to a Gallium Bis-Amido Complex: Imitation of Transition-Metal-Based Catalytic Systems

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Addition of Alkynes to a Gallium Bis-Amido Complex: Imitation of Transition-Metal-Based Catalytic Systems

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Morozov, Alexander G. Cherkasov, Anton V. Nikipelov, Alexander S. Fedushkin, Igor L. Skatova, Alexandra A. Abakumov, Gleb A.
Description	Author Affiliation: Fedushkin IL ( Institute of Organometallic Chemistry, Russian Academy of Sciences, Tropinina 49, 603950 Nizhny Novgorod, Russia. igorfed@iomc.ras.ru)
Abstract	Acetylene, phenylacetylene, and alkylbutynoates add reversibly to (dpp-bian)Ga–Ga(dpp-bian) (dpp-bian=1,2-bis[(2,6-diisopropylphenyl)-imino]acenaphthene) to give addition products $[dpp-bian(R^{1}CCR^{2})]Ga–Ga[(R^{2}CCR^{1})dpp-bian].$ The alkyne adds across the GaNC section, which results in new carbon–carbon and carbon–gallium bonds. The adducts were characterized by electron absorption, IR, and $^{1}H NMR$ spectroscopy and their molecular structures have been determined by single-crystal X-ray analysis. According to the X-ray data, a change in the coordination number of gallium from three [in (dpp-bian)Ga–Ga(dpp-bian)] to four (in the adducts) results in elongation of the metal–metal bond by approximately 0.13 Å. The adducts undergo a facile alkynes elimination at elevated temperatures. The equilibrium between [dpp-bian(PhCCH)]Ga–Ga[(HCCPh)dpp-bian] and [(dpp-bian)Ga–Ga(dpp-bian) + 2 PhCCH] in toluene solution was studied by $^{1}H NMR$ spectroscopy. The equilibrium constants at various temperatures (298≤T≤323 K) were determined, from which the thermodynamic parameters for the phenylacetylene elimination were calculated $(ΔG°=2.4 kJ mol^{−1},$ $ΔH°=46.0 kJ mol^{−1},$ $ΔS°=146.0 J K^{−1}mol^{−1}).$ The reactivity of (dpp-bian)Ga–Ga(dpp-bian) towards alkynes permits use as a catalyst for carbon–nitrogen and carbon–carbon bond-forming reactions. The bisgallium complex was found to be a highly effective catalyst for the hydroamination of phenylacetylene with anilines. For instance, with [(dpp-bian)Ga–Ga(dpp-bian)] (2 mol %) in benzene more than 99 % conversion of $PhNH_{2}$ and PhCCH into $PhNC(Ph)CH_{3}$ was achieved in 16 h at 90 °C. Under similar conditions, the reaction of 1-aminoanthracene with PhCCH catalyzed by (dpp-bian)Ga–Ga(dpp-bian) formed a carbon–carbon bond to afford 1-amino-2-(1-phenylvinyl)anthracene in 99 % yield.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	1
Volume Number	18
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2012-01-02
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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