Integration of Proximal Alkoxide and Lewis Acidic Cations To Boost Nickel-Catalyzed Borylation

Nickel catalysis offers a sustainable alternative to palladium catalysis for cross-coupling reactions, yet ligands tailored for nickel catalysis are lacking. We introduce new phosphine ligands designed to facilitate the incorporation of Lewis acidic cations. The combination of a phosphinoalcohol ligand with either (<i>n</i>-Bu)<sub>2</sub>Mg or KHMDS, as a source of Mg<sup>2+</sup> or K<sup>+</sup> cations respectively, proved to be optimal for the borylation of aryl chlorides. Studies verified that incorporation of Lewis acidic cations in the proximity of the Ni center enhances reactivity.

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Publication Details

Journal
Organic Letters
Published
2026-01-19
DOI
https://doi.org/10.1021/acs.orglett.5c05326
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

Integration of Proximal Alkoxide and Lewis Acidic Cations To Boost Nickel-Catalyzed Borylation

Jennifer A. Garden, Benjamin N. Bhawal, Benjamin S. Grills
Organic Letters
Catalytic Cross-Coupling Reactions
article

Integration of Proximal Alkoxide and Lewis Acidic Cations To Boost Nickel-Catalyzed Borylation

Jennifer A. Garden, Benjamin N. Bhawal, Benjamin S. Grills
article en

Abstract

Nickel catalysis offers a sustainable alternative to palladium catalysis for cross-coupling reactions, yet ligands tailored for nickel catalysis are lacking. We introduce new phosphine ligands designed to facilitate the incorporation of Lewis acidic cations. The combination of a phosphinoalcohol ligand with either (<i>n</i>-Bu)<sub>2</sub>Mg or KHMDS, as a source of Mg<sup>2+</sup> or K<sup>+</sup> cations respectively, proved to be optimal for the borylation of aryl chlorides. Studies verified that incorporation of Lewis acidic cations in the proximity of the Ni center enhances reactivity.

Organic LettersVol. 28(4)
University of Edinburgh (GB)
Responsible consumption and production
Openalex Percentile: Top 84%
Catalytic Cross-Coupling Reactions
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