Issue 20, 2024

The development of cage phosphine ‘DalPhos’ ligands to enable nickel-catalyzed cross-couplings of (hetero)aryl electrophiles

Abstract

Nickel-catalyzed cross-couplings of (hetero)aryl electrophiles with a diversity of nucleophiles (nitrogen, oxygen, carbon, and others) have evolved into competitive alternatives to well-established palladium- and copper-based protocols for the synthesis of (hetero)aryl products, including (hetero)anilines and (hetero)aryl ethers. A survey of the literature reveals that the use of cage phosphine (CgP) ‘DalPhos’ (DALhousie PHOSphine) bisphosphine-type ligands operating under thermal conditions currently offers the most broad substrate scope in nickel-catalyzed cross-couplings of this type, especially involving (hetero)aryl chlorides and phenol-derived electrophiles. The development and application of these DalPhos ligands is described in a ligand-specific manner that is intended to serve as a guide for the synthetic chemistry end-user.

Graphical abstract: The development of cage phosphine ‘DalPhos’ ligands to enable nickel-catalyzed cross-couplings of (hetero)aryl electrophiles

Article information

Article type
Perspective
Submitted
22 feb. 2024
Accepted
23 apr. 2024
First published
25 apr. 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 7394-7407

The development of cage phosphine ‘DalPhos’ ligands to enable nickel-catalyzed cross-couplings of (hetero)aryl electrophiles

K. M. Morrison and M. Stradiotto, Chem. Sci., 2024, 15, 7394 DOI: 10.1039/D4SC01253D

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