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Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent

Author

Listed:
  • Mingrui Li

    (Northeast Normal University)

  • Yingtao Wu

    (Northeast Normal University)

  • Xiao Song

    (Northeast Normal University)

  • Jiaqiong Sun

    (Northeast Normal University
    Northeast Normal University)

  • Zuxiao Zhang

    (University of Hawai’i at Mānoa. 2545 McCarthy Mall)

  • Guangfan Zheng

    (Northeast Normal University)

  • Qian Zhang

    (Northeast Normal University
    Chinese Academy of Sciences 345 Lingling Lu)

Abstract

The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis of nitrogen-containing compounds. However, bifunctional C–N reagents have never been employed in the carboamination of cyclopropane. In this study, we use an N-heterocyclic carbene (NHC), N-benzoyl saccharin, as a bifunctional reagent and a photoredox catalyst for a dual-catalyzed 1,3-aminoacylation of cyclopropane. NHCs play multiple roles, functioning as Lewis base catalysts to activate C–N bonds, promoting the oxidative quenching process of PC*, and acting as efficient acyl radical transfer catalysts for the formation of C–C bonds. The oxidative quenching process between the excited-state PC* and acyl NHC adduct is the key to the photooxidation generality of aryl cyclopropanes.

Suggested Citation

  • Mingrui Li & Yingtao Wu & Xiao Song & Jiaqiong Sun & Zuxiao Zhang & Guangfan Zheng & Qian Zhang, 2024. "Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-53202-8
    DOI: 10.1038/s41467-024-53202-8
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    References listed on IDEAS

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    1. Matthew N. Hopkinson & Christian Richter & Michael Schedler & Frank Glorius, 2014. "An overview of N-heterocyclic carbenes," Nature, Nature, vol. 510(7506), pages 485-496, June.
    2. Liang Ge & Chi Zhang & Chengkai Pan & Ding-Xing Wang & Dong-Ying Liu & Zhi-Qiang Li & Pingkang Shen & Lifang Tian & Chao Feng, 2022. "Photoredox-catalyzed C–C bond cleavage of cyclopropanes for the formation of C(sp3)–heteroatom bonds," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
    3. Zhouli Hu & Chenlong Wei & Qianqian Shi & Xianfang Hong & Jinhua Liu & Xiangui Zhou & Jinna Han & Wei Cao & Ashis Kumar Gupta & Xiaoxiang Zhang & Donghui Wei & Zhenqian Fu & Wei Huang, 2022. "Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    4. Liang Ge & Ding-Xing Wang & Renyi Xing & Di Ma & Patrick J. Walsh & Chao Feng, 2019. "Photoredox-catalyzed oxo-amination of aryl cyclopropanes," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    5. Shi-Chao Ren & Xing Yang & Bivas Mondal & Chengli Mou & Weiyi Tian & Zhichao Jin & Yonggui Robin Chi, 2022. "Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    6. You-Feng Han & Ying Huang & Hao Liu & Zhong-Hua Gao & Chun-Lin Zhang & Song Ye, 2022. "Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    7. Yonghoon Moon & Bohyun Park & Inwon Kim & Gyumin Kang & Sanghoon Shin & Dahye Kang & Mu-Hyun Baik & Sungwoo Hong, 2019. "Visible light induced alkene aminopyridylation using N-aminopyridinium salts as bifunctional reagents," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    8. Yuanyuan Xu & Hongwei Chen & Lu Yu & Xichao Peng & Jiawei Zhang & Zhongqiu Xing & Yuyan Bao & Aokun Liu & Yue Zhao & Changlin Tian & Yong Liang & Xiaoqiang Huang, 2024. "A light-driven enzymatic enantioselective radical acylation," Nature, Nature, vol. 625(7993), pages 74-78, January.
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