KIO4 -mediated Selective Hydroxymethylation/Methylenation of Imidazo-Heteroarenes: A Greener Approach.
Marcelo Straesser FrancoSumbal SabaJamal RafiqueAntonio Luiz BragaPublished in: Angewandte Chemie (International ed. in English) (2021)
Herein, we report a KIO4 -mediated, sustainable and chemoselective approach for the one-pot C(sp2 )-H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo[1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields.