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

preprint
submitted on 08.06.2020 and posted on 09.06.2020 by Yasuaki Morita, Bubwoong Kang, Rubi Nakashima, Yuki Shimizu, Asumi Sakai, Maiko Moriguchi, Yoko Yasuno, Tetsuya Satoh, Tetsuro Shinada, Masaki Kuse
We report a highly primary alcohol-selective aroylation reaction using N-aroylcarbazoles (NAroCs). The aroylation
proceeded 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.

History

Email Address of Submitting Author

kangb@pegasus.kobe-u.ac.jp

Institution

Kobe University

Country

Japan

ORCID For Submitting Author

0000-0003-3493-2132

Declaration of Conflict of Interest

no conflict of interest

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