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Pd-NHC catalyzed Suzuki cross-coupling of benzyl ammonium salts

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Abstract

A palladium-catalyzed Suzuki cross-coupling of benzyl ammonium triflates via activation of a Csp3–N bond to construct a Csp3–Csp2 bond is described. Various boronic acids can be coupled with a range of benzylamine-derived quaternary ammonium salts in 1:1 molar ratio by the bench-stable N-heterocyclic carbene palladium complex, SIPr-PdCl2-Py to afford diarylmethane derivatives. This reaction exhibits a wide substrate scope and functional group tolerance. Direct arylation of benzylamine in a one-pot process and the gram-scale reaction can be performed successfully.

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Acknowledgements

We are grateful to the National Natural Science Foundation of China (21571087) for the financial support.

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  1. Chuntao Zhong and Huiling Tang have been contributed equally to this article.

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  1. School of Chemistry and Material Science, Jiangsu Normal University, Xuzhou, 221116, China

    Chuntao Zhong, Huiling Tang, Benqiang Cui, Yanhui Shi & Changsheng Cao

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  1. Chuntao Zhong
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Zhong, C., Tang, H., Cui, B. et al. Pd-NHC catalyzed Suzuki cross-coupling of benzyl ammonium salts. Res Chem Intermed 48, 4017–4032 (2022). https://doi.org/10.1007/s11164-022-04795-6

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