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KIO 4 ‐mediated Selective Hydroxymethylation/Methylenation of Imidazo‐Heteroarenes: A Greener Approach
Author(s) -
Franco Marcelo Straesser,
Saba Sumbal,
Rafique Jamal,
Braga Antonio Luiz
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202104503
Subject(s) - ethylene glycol , chemistry , reagent , glycerol , hydroxymethyl , ethylene , formaldehyde , combinatorial chemistry , bond cleavage , organic chemistry , catalysis
Herein, we report a KIO 4 ‐mediated, sustainable and chemoselective approach for the one‐pot C(sp 2 )−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.