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A Diels–Alder Reaction Triggered by a [4 + 3] Metallacycloaddition

 

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Opened Access A Diels–Alder Reaction Triggered by a [4 + 3] Metallacycloaddition
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Author: Vivancos, Ángela
Vattier, Florencia
López Serrano, Joaquín
Paneque, Margarita
Poveda, Manuel L.
Álvarez González, Eleuterio
Department: Universidad de Sevilla. Departamento de Química Inorgánica
Date: 2015
Published in: Journal of the American Chemical Society, 137 (12), 4074-4077.
Document type: Article
Abstract: The TpMe2Ir(III) complex 1-OH2 (TpMe2 = hydrotris(3,5-dimethylpyrazolyl)borate), which contains a labile molecule of water and an iridium-bonded alkenyl moiety (−C(R)═C(R)–(R=CO2Me)) as part of a benzo-annulated five-membered iridacycle, reacts readily with the conjugated dienes butadiene and 2,3-dimethylbutadiene to afford the corresponding Diels–Alder products. Experimental and DFT studies are in accordance with an initial [4 + 3] cyclometalation reaction between the diene and the five-coordinated 16-electron organometallic fragment 1 (generated from 1-OH2 by facile water dissociation). The reaction can be extended to a related TpIr(III) complex (Tp = hydrotris(pyrazolyl)borate) that also features a labile ligand (i.e., 2-THF).
Cite: Vivancos, Á., Vattier, F., López Serrano, J., Paneque, M., Poveda, M.L. y Álvarez González, E. (2015). A Diels–Alder Reaction Triggered by a [4 + 3] Metallacycloaddition. Journal of the American Chemical Society, 137 (12), 4074-4077.
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URI: https://hdl.handle.net/11441/77993

DOI: 10.1021/jacs.5b01532

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