Sodium Iodide as a Catalyst in C-C Bond Forming Reactions

26 February 2007

1-bromo-1-nitroalkan-2-ols are used in the manufacture of photographic and ink-based materials, possibly because of their biocidal and antimicrobial properties. The existing methods for the synthesis of these molecules are low-yielding and this prompted workers at the University of Oviedo, Spain to investigate alternative, cheaper methods. The group had previously used samarium iodide as a source of nitronate anions,(by reaction with bromonitromethane) for reacting with an aldehyde and were surprised when the reaction of sodium iodide gave a different result (J M Concellon,et al, Org Lett, 2006, 8(26), 5979-5982).

The reactions proceed in good yield to give 1-bromo-1-nitroalkan-2-ols. If the aldehyde contains a stereocentre, then a good de product is obtained, resulting in the control of three adjacent centers in one reaction.