Anionic, in Situ Generation of Formaldehyde: A Very Useful and Versatile Tool in Synthesis

Geoffrey Deguest (1) , Laurent Bischoff (1) , Corinne Fruit (1) , Francis Marsais (2)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 IRCOF - Institut de Chimie Organique Fine

A very simple, safe and powerful method for the in situ generation of formaldehyde at low temperature in anhydrous conditions is described. This new tool avoids the use of gaseous formaldehyde and is suitable for basic carbon nucleophiles which cannot be generated in aqueous reaction media. Various substrates, including organolithium reagents and enolates, underwent smooth hydroxymethylation showing the versatility of this process. A Wittig reaction was also carried out in high yield.

Domaines: Chimie; Chimie organique; Chimie thérapeutique; Radiochimie; Matériaux; Chimie inorganique; Catalyse

Geoffrey Deguest, Laurent Bischoff, Corinne Fruit, Francis Marsais. Anionic, in Situ Generation of Formaldehyde: A Very Useful and Versatile Tool in Synthesis. Organic Letters, 2007, 9 (6), pp.1165-1167. ⟨10.1021/ol070145b⟩. ⟨hal-02385033⟩