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An efficient functionalization approach of oxazoles by using Pd‐catalyzed cross‐coupling reactions is reported. Oxazolone formation and subsequent sulfamoylation in situ are facilitated by employing N,N‐diethylsulfamoyl imidazolium triflate. Cross‐couplings provide both oxazole‐arenes and oxazole‐heteroarenes and were compatible with sensitive and epimerization‐prone substrates, as exemplified by the total synthesis of the natural product almazole D.