Cross-Coupling Reactions with Nickel, Visible Light, and tert-Butylamine as a Bifunctional Additive DOI Creative Commons
Jonas Düker,

Maximilian Philipp,

Thomas Lentner

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(2), P. 817 - 827

Published: Dec. 27, 2024

Transition metal catalysis is crucial for the synthesis of complex molecules, with ligands and bases playing a pivotal role in optimizing cross-coupling reactions. Despite advancements ligand design base selection, achieving effective synergy between these components remains challenging. We present here general approach to nickel-catalyzed photoredox reactions employing tert-butylamine as cost-effective bifunctional additive, acting ligand. This method proves C-O C-N bond-forming diverse array nucleophiles, including phenols, aliphatic alcohols, anilines, sulfonamides, sulfoximines, imines. Notably, protocol demonstrates significant applicability biomolecule derivatization facilitates sequential one-pot functionalizations. Spectroscopic investigations revealed robustness dynamic catalytic system, while elucidation structure-reactivity relationships demonstrated how computed molecular properties both nucleophile electrophile correlated reaction performance, providing foundation outcome prediction.

Language: Английский

Cross-Coupling Reactions with Nickel, Visible Light, and tert-Butylamine as a Bifunctional Additive DOI Creative Commons
Jonas Düker,

Maximilian Philipp,

Thomas Lentner

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(2), P. 817 - 827

Published: Dec. 27, 2024

Transition metal catalysis is crucial for the synthesis of complex molecules, with ligands and bases playing a pivotal role in optimizing cross-coupling reactions. Despite advancements ligand design base selection, achieving effective synergy between these components remains challenging. We present here general approach to nickel-catalyzed photoredox reactions employing tert-butylamine as cost-effective bifunctional additive, acting ligand. This method proves C-O C-N bond-forming diverse array nucleophiles, including phenols, aliphatic alcohols, anilines, sulfonamides, sulfoximines, imines. Notably, protocol demonstrates significant applicability biomolecule derivatization facilitates sequential one-pot functionalizations. Spectroscopic investigations revealed robustness dynamic catalytic system, while elucidation structure-reactivity relationships demonstrated how computed molecular properties both nucleophile electrophile correlated reaction performance, providing foundation outcome prediction.

Language: Английский

Citations

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