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Pd-catalyzed diastereoselective 1,1-diarylation of 1,1-disubstituted alkenes enabling the modular synthesis of 1,1,2,2-tetraarylethanes

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Abstract

The highly diastereoselective dicarbofunctionalization of substituted olefins still remains a daunting challenge in synthetic chemistry. Herein, we report a Pd-catalyzed diastereoselective 1,1-diarylation of 1,1-diarylethylene with chelation group free to enable the modular synthesis of smart material candidates, 1,1,2,2-tetraarylethanes (TAEs), which represent the first protocol by assembling four different aryl groups into ethane motif. Preliminary mechanistic experiments suggest that the crucial Pd-H species generated in situ do not disengage from the alkene intermediate during the reaction.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22171079), the Natural Science Foundation of Shanghai (21ZR1480400), the Shanghai Rising-Star Program (20QA1402300), the Shanghai Municipal Science and Technology Major Project (2018SHZDZX03), the Program of Introducing Talents of Discipline to Universities (B16017), the Fundamental Research Funds for the Central Universities. Y.C. thanks Prof. Weijun Zhao (East China University of Science and Technology) for insightful discussion. The authors thank the Analysis and Testing Center of East China University of Science and Technology for help with NMR analysis.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai, 200237, China

    Chengxi Zhang, Yang Xi, Jingping Qu & Yifeng Chen

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  1. Chengxi Zhang
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  2. Yang Xi
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Correspondence to Yifeng Chen.

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Supporting information The supporting information is available online at chem.scichina.com and link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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11426_2023_1780_MOESM1_ESM.pdf

Pd-catalyzed diastereoselective 1,1-diarylation of 1,1-disubstituted alkenes enabling the modular synthesis of 1,1,2,2-tetraarylethanes

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Zhang, C., Xi, Y., Qu, J. et al. Pd-catalyzed diastereoselective 1,1-diarylation of 1,1-disubstituted alkenes enabling the modular synthesis of 1,1,2,2-tetraarylethanes. Sci. China Chem. 66, 3539–3545 (2023). https://doi.org/10.1007/s11426-023-1780-2

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