L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols

A novel catalytic system based on L-proline N-oxide/CuI was developed and applied to the cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides. This strategy featured in the employment of an L-proline derived dihydrazides N-oxide compound as the superior supporting ligand. By using this protocol, a variety of products, including N-arylimidazoles, N-arylpyrazoles, N-arylpyrroles, N-arylamines, and aryl ethers, were synthesized with up to 99% yield. (C) 2020 Elsevier Ltd. All rights reserved.

Automated summary

A novel catalytic system based on L-proline N-oxide/CuI was developed and successfully applied to cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides, achieving high yields of up to 99% in synthesizing a variety of products.