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Mild Organic Base-Catalyzed Primary Alcohol-Selective Aroylation Reaction Using N-Aroylcarbazoles for Underexplored Prodrugs

We report a highly primary alcohol-selective aroylation reaction using N-aroylcarbazoles (NAroCs). The aroylationproceeded smoothly in the presence of DBU, which most likely works as a general base catalyst in the reaction system. The synthetic utility was displayed in the primary alcohol-selective aroylation of complex drug molecules and natural products to their prodrugs. Stoichiometrically generated carbazole, the starting material of NAroCs could be easily recovered. We also established safer multigram and multidecagram scale preparation methods of NAroCs, which are easy-to-handle bench-stable reagents.