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Enantioselective Friedel-Crafts alkylations catalysed by well-defined iridium and rhodium half-sandwich complexes

AuthorsCarmona, Daniel ; Lamata, M. Pilar ; Sánchez, Antonio; Viguri, Fernando ; Oro, Luis A.
Issue Date2011
CitationTetrahedron: Asymmetry 22(8): 893-906 (2011)
AbstractAqua-complexes (SM,RC)-[CpM{(R)-prophos}(H 2O)][SbF6]2 (M = Rh 1, Ir 2) catalysed the alkylation of α,β-unsaturated aldehydes with aromatics and heteroaromatics but in some cases, mixtures of products were obtained. Complexes 1 and 2 were also used to activate nitroalkenes for the Friedel-Crafts alkylation of a variety of aromatics and heteroaromatics, in particular, 1,3,5-trimethoxybenzene. For this substrate, the monoalkylated adduct was obtained in quantitative yield with enantioselectivities of up to 73% ee being achieved. The intermediate catalyst/nitroalkene was isolated and characterized and the complex catalyst/adduct was detected spectroscopically. From these data a plausible catalytic cycle is proposed. © 2011 Elsevier Ltd. All rights reserved.
Identifiersdoi: 10.1016/j.tetasy.2011.05.003
issn: 0957-4166
Appears in Collections:(ICMA) Artículos
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