KIO4-mediated selective hydroxymethylation/methylenation of imidazo-heteroarenes: a greener approach
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2022
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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.
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C(sp2)−H functionalization, Green chemistry, Hydroxymethylation, Imidazo-heteroarenes, KIO4
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FRANCO, Marcelo Straesser et al. KIO4-mediated selective hydroxymethylation/methylenation of Imidazo-heteroarenes: a greener approach. Angewandte Chemie International, Weinheim, v. 60, n. 34, p. 18454-18460, 2021. DOI: 10.1002/anie.202104503. Disponível em: https://onlinelibrary.wiley.com/doi/10.1002/anie.202104503. Acesso em: 31 jul. 2024.