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Palladium-catalyzed ortho-C-H silylation of biaryl aldehydes using a transient directing group

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Abstract

A strategy for Pd-catalyzed ortho-C-H silylation of biaryl aldehydes enabled by a transient auxiliary is presented. This protocol provides a broad range of ortho-silylated biaryl aldehydes in good yields. The silyl moiety can be further functionalized under mild conditions, rendering the silylated products useful building blocks. Notably, this protocol also offers an opportunity to establish a platform for expeditious synthesis of structurally diverse axially chiral biaryl aldehydes via sequential atroposelective interannular C-H functionalization/intraanular C-H silylation.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21925109, 21772170), the Outstanding Young Talents of Zhejiang Province High-level Personnel of Special Support (ZJWR0108), the Fundamental Research Funds for the Central Universities (2018XZZX001-02) and Zhejiang Provincial Natural Science Foundation (LR17B020001).

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Authors and Affiliations

  1. Department of Chemistry, Zhejiang University, Hangzhou, 310027, China

    Yong-Jie Wu, Qi-Jun Yao, Gang Liao & Bing-Feng Shi

  2. School of Chemical & Environmental Engineering, Wuyi University, Jiangmen, 529020, China

    Hao-Ming Chen

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  1. Yong-Jie Wu
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  2. Qi-Jun Yao
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  3. Hao-Ming Chen
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  4. Gang Liao
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  5. Bing-Feng Shi
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Correspondence to Bing-Feng Shi.

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Wu, YJ., Yao, QJ., Chen, HM. et al. Palladium-catalyzed ortho-C-H silylation of biaryl aldehydes using a transient directing group. Sci. China Chem. 63, 875–880 (2020). https://doi.org/10.1007/s11426-020-9694-3

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