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Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction

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Abstract

The first system controlled anomeric isomerism of glucopyranoside-functionalized N-heterocyclic carbenes based pyridine enhanced precatalyst preparation, stabilization and initiation type palladium(II) complexes (Glu-NHCs-Pd(II)-PEPPSI, 2a–d) were prepared and fully characterized. It is interesting to note that pure β–anomer PEPPSI complex 2d was obtained, in which the Glu-substituent connects to the imidazole heterocycle ring N through ethoxy bridged anomeric carbon. In addition, the catalytic activities revealed that Glu-NHCs-Pd(II)-PEPPSI complexes 2a-d are efficient catalysts for the aqueous Suzuki reaction. Under optimized conditions, a series of fluorene-cored functional materials with different aryl-substituents were synthesized through the Suzuki reaction with excellent yields. The Glu-NHCs-Pd(II)-PEPPSI complex containing bulky and rigid 2,5-dimethylphenyl group played an important role in maintaining the β conformation and improving the catalytic activity significantly.

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CCDC Deposition Number 2069632 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (No. 21562002), the Funding Project for Academic and Technical Leaders of Jiangxi Province (No. 20172BCB22021), Education Department of Jiangxi Province (No. GJJ201427, GJJ201424) and Graduate Innovation Fund of Gannan Normal University (No. YCX20A008).

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  1. Key Laboratory of Jiangxi University for Functional Materials Chemistry, College of Chemistry and Chemical Engineering, Gannan Normal University, 341000, Ganzhou, People’s Republic of China

    Zhonggao Zhou, Qian Xie, Jing Li, Yangyang Yuan, Yong Liu, Yulong Liu, Dongliang Lu & Yongrong Xie

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Zhou, Z., Xie, Q., Li, J. et al. Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction. Catal Lett 152, 838–847 (2022). https://doi.org/10.1007/s10562-021-03654-0

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