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Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis

Author

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  • Xiaokai Cheng

    (Zhejiang University)

  • Huangzhe Lu

    (Zhejiang University)

  • Zhan Lu

    (Zhejiang University)

Abstract

The asymmetric cross-coupling reaction is developed as a straightforward strategy toward 1,1-diaryl alkanes, which are a key skeleton in a series of natural products and bioactive molecules in recent years. Here we report an enantioselective benzylic C(sp3)−H bond arylation via photoredox/nickel dual catalysis. Sterically hindered chiral biimidazoline ligands are designed for this asymmetric cross-coupling reaction. Readily available alkyl benzenes and aryl bromides with various functional groups tolerance can be easily and directly transferred to useful chiral 1,1-diaryl alkanes including pharmaceutical intermediates and bioactive molecules. This reaction proceeds smoothly under mild conditions without the use of external redox reagents.

Suggested Citation

  • Xiaokai Cheng & Huangzhe Lu & Zhan Lu, 2019. "Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11392-6
    DOI: 10.1038/s41467-019-11392-6
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    Cited by:

    1. Li-Li Zhang & Yu-Zhong Gao & Sheng-Han Cai & Hui Yu & Shou-Jie Shen & Qian Ping & Ze-Peng Yang, 2024. "Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    2. Yantao Li & Qianzhen Shao & Hengchi He & Chengjian Zhu & Xiao-Song Xue & Jin Xie, 2022. "Highly selective synthesis of all-carbon tetrasubstituted alkenes by deoxygenative alkenylation of carboxylic acids," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    3. Dong Liu & Zhao-Ran Liu & Zhen-Hua Wang & Cong Ma & Simon Herbert & Hartmut Schirok & Tian-Sheng Mei, 2022. "Paired electrolysis-enabled nickel-catalyzed enantioselective reductive cross-coupling between α-chloroesters and aryl bromides," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    4. Liang Jin & Ya Li & Yihui Mao & Xiao-Bao He & Zhan Lu & Qi Zhang & Bing-Feng Shi, 2024. "Chiral dinitrogen ligand enabled asymmetric Pd/norbornene cooperative catalysis toward the assembly of C–N axially chiral scaffolds," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    5. Xiaomin Shu & De Zhong & Qian Huang & Leitao Huan & Haohua Huo, 2023. "Site- and enantioselective cross-coupling of saturated N-heterocycles with carboxylic acids by cooperative Ni/photoredox catalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    6. Yun-Zhao Wang & Zhen-Hua Wang & Inbal L. Eshel & Bing Sun & Dong Liu & Yu-Cheng Gu & Anat Milo & Tian-Sheng Mei, 2023. "Nickel/biimidazole-catalyzed electrochemical enantioselective reductive cross-coupling of aryl aziridines with aryl iodides," Nature Communications, Nature, vol. 14(1), pages 1-10, December.

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