Easily Accessible and Solution-Stable Ni(0) Precatalysts for High-Throughput Experimentation

Overview

Journal Chemistry

Date 2025 Jan 17

PMID 39822108

Authors

Gilian T Thomas

Odhran D Cruise

Daelin Peel-Smith

Nahiane Pipaon Fernandez

Charles Killeen

David C Leitch

Affiliations

Soon will be listed here.

Abstract

We report the synthesis, characterization, and catalytic applications of N,N'-diaryl diazabutadiene (DAB) Ni(0) complexes stabilized by alkene ligands. These complexes are soluble and stable in several organic solvents, making them ideal candidates for in situ catalyst formation during high-throughput experimentation (HTE). We used HTE to evaluate these Ni(0) precatalysts in a variety of Suzuki and C-N coupling reactions, and they were found to have equal or better performance than the still-standard Ni(0) source, Ni(COD).

Citing Articles

Easily Accessible and Solution-Stable Ni(0) Precatalysts for High-Throughput Experimentation.

Thomas G, Cruise O, Peel-Smith D, Fernandez N, Killeen C, Leitch D Chemistry. 2025; 31(12):e202403960.

PMID: 39822108 PMC: 11855265. DOI: 10.1002/chem.202403960.

References

Tasker S, Standley E, Jamison T . Recent advances in homogeneous nickel catalysis. Nature. 2014; 509(7500):299-309. PMC: 4344729. DOI: 10.1038/nature13274. View

Kim S, Goldfogel M, Gilbert M, Weix D . Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides. J Am Chem Soc. 2020; 142(22):9902-9907. PMC: 7418462. DOI: 10.1021/jacs.0c02673. View

Shields J, Gray E, Doyle A . A modular, air-stable nickel precatalyst. Org Lett. 2015; 17(9):2166-9. PMC: 4719147. DOI: 10.1021/acs.orglett.5b00766. View

Tran V, Kim H . Facile tin(II)-catalyzed synthesis of -heterocycles from dicarboxylic acids and arylamines. Org Biomol Chem. 2022; 20(14):2881-2888. DOI: 10.1039/d2ob00330a. View

Kang K, Huang L, Weix D . Sulfonate Versus Sulfonate: Nickel and Palladium Multimetallic Cross-Electrophile Coupling of Aryl Triflates with Aryl Tosylates. J Am Chem Soc. 2020; 142(24):10634-10640. PMC: 7373434. DOI: 10.1021/jacs.0c04670. View

Sgro M, Stephan D . Synthesis and exchange reactions of Ni-dimine-COD, acetylene and olefin complexes. Dalton Trans. 2010; 39(25):5786-94. DOI: 10.1039/c001312a. View

Dander J, Weires N, Garg N . Benchtop Delivery of Ni(cod)2 using Paraffin Capsules. Org Lett. 2016; 18(15):3934-6. PMC: 7010371. DOI: 10.1021/acs.orglett.6b01758. View

Liang A, Wang K, Gao Y, Finkenauer B, Zhu C, Jin L . Highly Efficient Halide Perovskite Light-Emitting Diodes via Molecular Passivation. Angew Chem Int Ed Engl. 2021; 60(15):8337-8343. DOI: 10.1002/anie.202100243. View

Wang Z, Ma Q, Li R, Shao L . Palladium-catalyzed Suzuki-Miyaura coupling of aryl sulfamates with arylboronic acids. Org Biomol Chem. 2013; 11(45):7899-906. DOI: 10.1039/c3ob41382a. View

10.

Weber J, Longstreet A, Jamison T . Bench-Stable Nickel Precatalysts with Heck-type Activation. Organometallics. 2018; 37(16):2716-2722. PMC: 6113681. DOI: 10.1021/acs.organomet.8b00351. View

11.

Thomas G, Cruise O, Peel-Smith D, Fernandez N, Killeen C, Leitch D . Easily Accessible and Solution-Stable Ni(0) Precatalysts for High-Throughput Experimentation. Chemistry. 2025; 31(12):e202403960. PMC: 11855265. DOI: 10.1002/chem.202403960. View

12.

Reeves E, Humke J, Neufeldt S . N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki-Miyaura Cross Coupling. J Org Chem. 2019; 84(18):11799-11812. PMC: 6754280. DOI: 10.1021/acs.joc.9b01692. View

13.

Newman-Stonebraker S, Wang J, Jeffrey P, Doyle A . Structure-Reactivity Relationships of Buchwald-Type Phosphines in Nickel-Catalyzed Cross-Couplings. J Am Chem Soc. 2022; 144(42):19635-19648. PMC: 10276769. DOI: 10.1021/jacs.2c09840. View

14.

Hazari N, Melvin P, Beromi M . Well-defined nickel and palladium precatalysts for cross-coupling. Nat Rev Chem. 2017; 1. PMC: 5637737. DOI: 10.1038/s41570-017-0025. View

15.

Rubel C, He W, Wisniewski S, Engle K . Benchtop Nickel Catalysis Invigorated by Electron-Deficient Diene Ligands. Acc Chem Res. 2024; 57(3):312-326. DOI: 10.1021/acs.accounts.3c00638. View

16.

Nett A, Canellas S, Higuchi Y, Robo M, Kochkodan J, Haynes 2nd M . Stable, Well-Defined Nickel(0) Catalysts for Catalytic C-C and C-N Bond Formation. ACS Catal. 2018; 8(7):6606-6611. PMC: 6071431. DOI: 10.1021/acscatal.8b02187. View

17.

Saeb R, Boulenger B, Cornella J . "Naked Nickel"-Catalyzed Amination of Heteroaryl Bromides. Org Lett. 2024; 26(28):5928-5933. PMC: 11267598. DOI: 10.1021/acs.orglett.4c01738. View

18.

Tran V, Li Z, Apolinar O, Derosa J, Joannou M, Wisniewski S . Ni(COD)(DQ): An Air-Stable 18-Electron Nickel(0)-Olefin Precatalyst. Angew Chem Int Ed Engl. 2020; 59(19):7409-7413. DOI: 10.1002/anie.202000124. View

19.

Mehta M, Boit T, Dander J, Garg N . Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of Aliphatic Amides on the Benchtop. Org Lett. 2019; 22(1):1-5. PMC: 6994262. DOI: 10.1021/acs.orglett.9b03434. View