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Please use this identifier to cite or link to this item: http://ir.ncue.edu.tw/ir/handle/987654321/14783

Title: Insertion, Reduction, and Carbon-carbon Coupling Induced by Monomeric Aluminum Hydride Compounds Bearing Substituted Pyrrolyl Ligands
Authors: Lin, Che-Yu;Tsai, Chia-Fu;Chen, Hsing-Jen;Hung, Chen-Hsiung;Yu, Ru-Ching;Kuo, Pei-Cheng;Lee, Hon-Man;Huang, Jui-Hsien
Contributors: 化學系
Keywords: Aluminum hydride;C-C coupling;Insertion;Pyrrole
Date: 2006-04
Issue Date: 2012-12-10T01:39:44Z
Publisher: WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Abstract: A monomeric aluminum hydride complex bearing substituted pyrrolyl ligands, AlH[C4H3N(CH2NMe2)-2]2 (1), was synthesized and structurally characterized. To further confirm the presence of AlH bonds, the compound AlD[C4H3N(CH2NMe2)-2]2 ([D]1) was synthesized by reacting LiAlD4 with [C4H4N(CH2NMe2)-2]. Compound 1 and [D]1 react with phenyl isothiocyanate yielding Al[C4H3N(CH2NMe2)-2]2[η3-SCHNPh] (2) and Al[C4H3N(CH2NMe2)-2]2[η3-SCDNPh] ([D]2) by insertion. The reactions of 1 with 9-fluorenone and benzophenone generated the unusual aluminum alkoxide complexes 3 and 4, respectively, through intramolecular proton abstraction and C–C coupling. A mechanistic study shows that 9-fluorenone coordinates to [D]1 and releases one equivalent of HD followed by C–C coupling and hydride transfer to yield the final product. Reduction of benzil with 1 affords aluminum enediolate complex 5 in moderate yield. Mechanistic studies also showed that the benzil was inserted into the aluminum hydride bond of [D]1 through hydroalumination followed by proton transfer to generate the final product [D]5. All new complexes have been characterized by 1H and 13C NMR spectroscopy and X-ray crystallography.
Relation: Chemistry-A European Journal, 12(11): 3067-3073
Appears in Collections:[Department of Chemistry] Periodical Articles

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