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Título

Efficient Rhodium-catalyzed multicomponent reaction for the synthesis of novel propargylamines

AutorRubio-Pérez, Laura ; Iglesias, Manuel ; Munárriz, Julen; Polo, Víctor; Pérez-Torrente, Jesús J. ; Oro, Luis A.
Palabras claveC-H activation
Multicomponent reactions
Hydroalkynylation
Propargylamines
Rrhodium
Fecha de publicación2015
EditorWiley-VCH
CitaciónChemistry - A European Journal 21(49): 17701-17707 (2015)
Resumen[{Rh(μ-Cl)(H)2(IPr)}2] (IPr = 1,3-bis-(2,6-diisopropylphenyl)imidazole-2-ylidene) was found to be an efficient catalyst for the synthesis of novel propargylamines by a one-pot three-component reaction between primary arylamines, aliphatic aldehydes, and triisopropylsilylacetylene. This methodology offers an efficient synthetic pathway for the preparation of secondary propargylamines derived from aliphatic aldehydes. The reactivity of [{Rh(μ-Cl)(H)2(IPr)}2] with amines and aldehydes was studied, leading to the identification of complexes [RhCl(CO)IPr(MesNH2)] (MesNH2 = 2,4,6-trimethylaniline) and [RhCl(CO)2IPr]. The latter shows a very low catalytic activity while the former brought about reaction rates similar to those obtained with [{Rh(μ-Cl)(H)2(IPr)}2]. Besides, complex [RhCl(CO)IPr(MesNH2)] reacts with an excess of amine and aldehyde to give [RhCl(CO)IPr{MesN[DOUBLE BOND]CHCH2CH(CH3)2}], which was postulated as the active species. A mechanism that clarifies the scarcely studied catalytic cycle of A3-coupling reactions is proposed based on reactivity studies and DFT calculations.
Versión del editorhttp://dx.doi.org/10.1002/chem.201502993
URIhttp://hdl.handle.net/10261/133799
DOI10.1002/chem.201502993
Identificadoresdoi: 10.1002/chem.201502993
e-issn: 1521-3765
issn: 0947-6539
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