Issue 17, 2023

Recent advances in the application of ligands in palladium-catalyzed chemoselective coupling reactions at C–Br, C–OTf, and C–Cl sites

Abstract

This article provides an overview of the development of palladium-catalyzed coupling reactions and the effects of ligand properties on the chemoselectivity of aryl (pseudo)halides. The selectivity of coupling reactions can be significantly influenced by applying appropriate ligands. This review discusses the chemoselectivity of triaryl and trialkyl phosphines, Pd(I) dimers, Buchwald-type phosphines, bidentate phosphine ligands, CataCXium phosphine ligands, SelectPhos, YPhos, and N-heterocyclic carbene catalysts. In each section, the properties of specific catalysts are described along with the chemoselectivity of reactions applying these ligand systems. Successful sequential chemoselective coupling approaches are presented as examples to demonstrate the capacity of catalysts to regulate chemoselectivity in coupling reactions, with significant implications for synthesizing pharmaceuticals, materials, and other valuable compounds.

Graphical abstract: Recent advances in the application of ligands in palladium-catalyzed chemoselective coupling reactions at C–Br, C–OTf, and C–Cl sites

Article information

Article type
Review Article
Submitted
28 apr 2023
Accepted
04 jun 2023
First published
16 jun 2023

Org. Chem. Front., 2023,10, 4408-4436

Recent advances in the application of ligands in palladium-catalyzed chemoselective coupling reactions at C–Br, C–OTf, and C–Cl sites

S. S. Ng, W. H. Pang, O. Y. Yuen and C. M. So, Org. Chem. Front., 2023, 10, 4408 DOI: 10.1039/D3QO00640A

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