Nickel() complexes containing tridentate ONC ligands (i = abnormal N-heterocyclic carbene donors) and their catalytic application in Suzuki-Miyaura coupling reaction

New nickel complexes with tridentate phenoxy-amidate-aNHC donor groups were synthesized from the reactions between nickel acetate and imidazolium ligand precursors in net pyridine. An unusual degradation pathway was observed, leading to imidazole derivatives occupying the fourth coordination sites i...

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Published inDalton transactions : an international journal of inorganic chemistry Vol. 51; no. 17; pp. 6663 - 6672
Main Authors Lee, Jhen-Yi, Hsieh, Meng-Jun, Ho, Tsai-En, Wu, Bo-Hsin, Lee, Hon Man
Format Journal Article
Published 03.05.2022
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Summary:New nickel complexes with tridentate phenoxy-amidate-aNHC donor groups were synthesized from the reactions between nickel acetate and imidazolium ligand precursors in net pyridine. An unusual degradation pathway was observed, leading to imidazole derivatives occupying the fourth coordination sites in these square planar complexes. A new imidazole-coordinated nickel complex was found to be efficient in catalyzing Suzuki-Miyaura cross-coupling with aryl chlorides under 3 mol% of catalyst loading. The catalytic activities were superior to those of its reported normal NHC counterpart. Instead of the common procedure of using additional phosphine, the addition of IMes·HCl significantly enhances the product yields of the catalytic reaction. A Ni( ii ) complex with tridentate phenoxy-amidate-aNHC donors was synthesized, which was efficient in Suzuki-Miyaura coupling with additional IMes·HCl.
Bibliography:3c
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For ESI and crystallographic data in CIF or other electronic format see DOI
2100760
H NMR assignment of coupled products, NMR spectra of ligand precursors, nickel complexes and coupled products. CCDC
2100761
https://doi.org/10.1039/d1dt04114b
and
Electronic supplementary information (ESI) available: Additional schemes, procedure for X-ray structural studies, crystallographic data, molecular structure of
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2100759
ISSN:1477-9226
1477-9234
DOI:10.1039/d1dt04114b