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Copper/Nitroxyl-Catalyzed Synthesis of Pyrroles by Oxidative Coupling of Diols and Primary Amines at Room Temperature

Weiru Fu, Lina Zhu, Shangzhi Tan, Zhengjia Zhao, Xiangzhu Yu and Lianyue Wang*

*College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China, Email: lianyuewanglnnu.edu.cn

W. Fu, L. Zhu, S. Tan, Z. Zhao, X. Yu, L. Wang, J. Org. Chem., 2022, 87, 13389-13395.

DOI: 10.1021/acs.joc.2c01646


Abstract

A Cu/ABNO-catalyzed aerobic oxidative coupling of diols and a broad range of primary amines provides N-substituted pyrroles. The reaction proceeds at room temperature with an O2 balloon as the oxidant using commercially available materials as the substrates and catalysts. The catalyst system offers a good tolerance to sensitive functional groups.

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proposed reaction pathway



Key Words

pyrroles, ABNO, oxygen


ID: J42-Y2022