1,5-Diaza-3,7-diphosphacyclooctanes (P2N2): An Underappreciated Ligand Class for Nickel- and Palladium-Catalyzed Heck-Type Cross-Couplings

Eric S. Isbrandt; Stephen G. Newman

doi:10.1055/s-0043-1775400

Synlett, Table of Contents

Synlett 2025; 36(06): 607-614
DOI: 10.1055/s-0043-1775400

synpacts

1,5-Diaza-3,7-diphosphacyclooctanes (P₂N₂): An Underappreciated Ligand Class for Nickel- and Palladium-Catalyzed Heck-Type Cross-Couplings

Eric S. Isbrandt

,

Stephen G. Newman ∗

Abstract

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Abstract

1,5-Diaza-3,7-diphosphacyclooctane (P₂N₂) scaffolds represent a readily accessible, tunable ligand class for transition metals. However, despite their prevalence in areas such as electrocatalysis and coordination chemistry, P₂N₂ ligands have been rarely used to make catalysts for organic synthesis. Research into Mizoroki–Heck-type aldehyde, alcohol, and alkene arylation reactions has revealed that the P₂N₂ family outperforms many commonly used phosphines. This Synpacts article summarizes our work and provides a broad overview on the preparation and application of P₂N₂ ligands in organic synthesis. It also serves to highlight how a simple, modular class of ligands can solve contemporary challenges with transition-metal catalysis, including novel reactivity and exceptional regioselectivity.

Key words

transition-metal catalysis - Mizoroki–Heck coupling - ligand design - regioselectivity - reductive cross-coupling

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References

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