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Chemical Science

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

Kathleen M. Morrisona  and  Mark Stradiotto ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Dalhousie University, 6274 Coburg Road, P.O. 15000, Halifax, Nova Scotia B3H 4R2, Canada
E-mail: mark.stradiotto@dal.ca

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

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Article information

DOI
https://doi.org/10.1039/D4SC01253D
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, Advance Article

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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, Advance Article , DOI: 10.1039/D4SC01253D

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