Unprecedentedly mild direct Pd-catalyzed arylation of oxazolo[4,5-b]pyridine

Pd-catalyzed C-2 arylation of oxazolo4,5-b]pyridine proceeds efficiently at 30 °C and tolerates a variety of aryl halides, including derivatized amino acids for which no racemization was observed during the reaction. Experimental evidence for facile deprotonation of oxazolo4,5-b]pyridine under the reaction conditions is presented and the nature of the anionic intermediates is computationally examined.