Radical cascade synthesis of azoles via tandem hydrogen atom transfer† † Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc06239d

ABSTRACT: A radical cascade strategy for the modular synthesis of five-membered heteroarenes (e.g. oxazoles, imidazoles) from feedstock reagents (e.g. alcohols, amines, nitriles) has been developed. This double C–H oxidation is enabled by in situ generated imidate and acyloxy radicals, which afford regio- and chemo-selective β C–H bis-functionalization. The broad synthetic utility of this tandem hydrogen atom transfer (HAT) approach to access azoles is included, along with experiments and computations that provide insight into the selectivity and mechanism of both HAT events. A radical cascade enables rapid, modular access to five-membered heteroarenes, including oxazoles and imidazoles, through a regio- and chemo-selective β C–H bis-functionalization.

SUBMITTER: Chen A 

PROVIDER: S-EPMC8157396 | biostudies-literature |

REPOSITORIES: biostudies-literature