Room-Temperature CuI-Catalyzed N-Arylation of Cyclopropylamine

J Org Chem. 2024 Jan 5;89(1):57-67. doi: 10.1021/acs.joc.3c01357. Epub 2023 Dec 18.

Abstract

A general and efficient CuI/N-carbazolyl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the N-arylation of cyclopropylamine using aryl bromides at room temperature. Herein, 5 mol % CuI and 5 mol % of the ligand were used to synthesize N-aryl cyclopropylamines in moderate to excellent yields. This protocol was scaled up to produce the desired product at gram levels and has been generalized for C-N coupling between aryl bromides and amines at room temperature.