The synthesis of oxazoles, which is often accomplished via two-electron chemistry, remains an enduring pursuit due to their importance in medicine and catalysis, and presence in natural products. We present a novel and complementary approach which leverages orthogonal one-electron chemistry to couple alcohols and nitriles to generate this oxidized heterocycle via an imidate intermediate. Our simple, two step method employs a β-selective C-H amination followed by in tandem mild oxidation of the resultant oxazoline. Combinatorial application of this streamlined strategy promises to provide libraries of previously inaccessible oxazoles of medicinal interest from simple feedstock reagents.

Radical coupling of feedstock alcohols and nitriles to access a library of oxazoles

255th National Meeting (2018)

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