Unprecedented rhodium-mediated catalytic transfer hydrogenation of a phosphonate functionalized olefin in ecofriendly media

摘要

RhCl3.xH(2)O catalyst-mediated hydrogenation reactions of vinyl phosphonic diethyl ester H2C=CH-P(O)(OEt)(2) (1) have been investigated. Results demonstrate that the hydrogenation of H2C=CH-P(O)(OEt)(2) (1) to CH3CH2-P(O)(OEt)(OH) (2) proceeds in the presence of RhCl3 (.) xH(2)O catalyst, without any external hydrogen source and ancillary ligands, to near qualitative yields in ethanol and water media. P-31, C-13 and H-1 NMR and deuterium-labeling experiments provide evidence for the non-concerted mechanistic pathway associated with the hydrogenation of 1 to 2. (C) 2004 Elsevier B.V. All rights reserved.