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Upgrading ketone synthesis direct from carboxylic acids and organohalides

Author

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  • Rehanguli Ruzi

    (Nanjing University)

  • Kai Liu

    (Nanjing University)

  • Chengjian Zhu

    (Nanjing University
    Zhengzhou University)

  • Jin Xie

    (Nanjing University)

Abstract

The ketone functional group has a unique reactivity in organic chemistry and is associated with a number of useful reactions. Catalytic methods for ketone synthesis are continually being developed. Here, we report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of commercially available chemicals, aromatic acids and aryl/alkyl bromides. This allows for concise synthesis of highly functionalized ketones directly, without the preparation of activated carbonyl intermediates or organometallic compounds, and thus complements the conventional Weinreb ketone synthesis. Use of the appropriate photocatalyst, ligand amount and solvents can match the reaction rate required by any simple catalytic cycle. The practicality and synthetic robustness of the reaction are illustrated by the facile synthesis of complex ketones from readily available feedstock chemicals.

Suggested Citation

  • Rehanguli Ruzi & Kai Liu & Chengjian Zhu & Jin Xie, 2020. "Upgrading ketone synthesis direct from carboxylic acids and organohalides," Nature Communications, Nature, vol. 11(1), pages 1-9, December.
  • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-17224-2
    DOI: 10.1038/s41467-020-17224-2
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    Cited by:

    1. Xinlong Ma & Haibin Yin & Zhengtian Pu & Xinyan Zhang & Sunpei Hu & Tao Zhou & Weizhe Gao & Laihao Luo & Hongliang Li & Jie Zeng, 2024. "Propane wet reforming over PtSn nanoparticles on γ-Al2O3 for acetone synthesis," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    2. Nian Li & Jinhang Li & Mingzhe Qin & Jiajun Li & Jie Han & Chengjian Zhu & Weipeng Li & Jin Xie, 2022. "Highly selective single and multiple deuteration of unactivated C(sp3)-H bonds," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    3. 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.
    4. Shuaishuai Wang & Tingrui Li & Chengyihan Gu & Jie Han & Chuan-Gang Zhao & Chengjian Zhu & Hairen Tan & Jin Xie, 2022. "Decarboxylative tandem C-N coupling with nitroarenes via SH2 mechanism," Nature Communications, Nature, vol. 13(1), pages 1-10, December.

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