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

Yasuaki Morita; Bubwoong Kang; Rubi Nakashima; Yuki Shimizu; Asumi Sakai; Maiko Moriguchi; Yoko Yasuno; Tetsuya Sato; Tetsuro Shinada; Masaki Kuse

doi:10.26434/chemrxiv.12444797.v1

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

Yasuaki Morita, Bubwoong Kang, Rubi Nakashima, Yuki Shimizu, Asumi Sakai, Maiko Moriguchi, Yoko Yasuno, Tetsuya Sato, Tetsuro Shinada, Masaki Kuse

Organic and Biological Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Journal	Unknown Journal
DOIs	https://doi.org/10.26434/chemrxiv.12444797.v1
Publication status	Published - Jun 8 2020

All Science Journal Classification (ASJC) codes

Chemistry(all)
Chemical Engineering(all)
Materials Science(all)

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Mild Organic Base-Catalyzed Primary Alcohol-Selective Aroylation Reaction Using N-Aroylcarbazoles for Underexplored Prodrugs. / Morita, Yasuaki; Kang, Bubwoong; Nakashima, Rubi; Shimizu, Yuki; Sakai, Asumi; Moriguchi, Maiko; Yasuno, Yoko; Sato, Tetsuya; Shinada, Tetsuro; Kuse, Masaki.

In: Unknown Journal, 08.06.2020.

Research output: Contribution to journal › Article › peer-review

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AU - Shimizu, Yuki

AU - Sakai, Asumi

AU - Moriguchi, Maiko

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AU - Kuse, Masaki

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