The activation of the CH bond in aldehydes promoted by acyl-rhodium (III) complexes is involved in many reactions such as decarbonylation or hydroacylation reactions. The hydroacylation is an interesting method to prepare ketones due to the availability of the starting materials. Herein, we report the synthesis and characterization of an alkyl-acyl-rhodium (III) and an hydrido-acyl-rhodium (III) compounds, which could be intermediates in the hydroacylation reaction. The reaction of [RhCl(Nbd)]2 (Nbd = norbornadiene) with quinoline-8-carbaldehyde (C9H6CNO) in presence of tris(p-fluorophenyl)phosphine, (PR3), gives [RhCl(C9H6NCO)(Nbyl)(PR3)] (Nbyl = norbornenyl). This alkyl-acyl-Rh(III) compound react with other equivalent of PR3 and an extra equivalent of Nbd to form [RhCl(C9H6NCO)(H)((p-FPh)3P)2] and one equivalent of 8-quinolinyl aleknyl ketone, which is a hydroacylation product. Moreover, these Rh(III) complexes have proved to be an efficient catalysts for hydroacylation reaction of quinoline-8-carbaldehyde with norbornadiene.

Norbornenyl-Acyl-Rhodium(III) complex as a likely intermediate in the catalytic hydroacylation of norbornadiene

253rd National Meeting (2017)

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