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Di-tert-butyl Peroxide-Mediated Radical C(sp2/sp3)–S Bond Cleavage and Group-Transfer Cyclization

  • Kai Luo
    Kai Luo
    Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China
    More by Kai Luo
  • Wen-Chao Yang
    Wen-Chao Yang
    Institute of Pesticide, School of Horticulture and Plant Protection, Yangzhou University, Yangzhou 225009, China
  • Kai Wei
    Kai Wei
    Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China
    More by Kai Wei
  • Yue Liu
    Yue Liu
    Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China
    More by Yue Liu
  • Jun-Ke Wang
    Jun-Ke Wang
    Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China
    More by Jun-Ke Wang
  • , and 
  • Lei Wu*
    Lei Wu
    Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China
    *E-mail: [email protected]
    More by Lei Wu
Cite this: Org. Lett. 2019, 21, 19, 7851–7856
Publication Date (Web):September 16, 2019
https://doi.org/10.1021/acs.orglett.9b02837
Copyright © 2019 American Chemical Society
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Abstract

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A novel strategy of cascade radical C(sp2/sp3)–S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b02837.

  • Experimental procedures and spectral data for all new compounds (PDF)

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Cited By


This article is cited by 14 publications.

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  2. Sitian Yuan, Xiaoling Ye, Jingyu Cai, Zhibin Song, Yuxing Tan, Yiyuan Peng, Qiuping Ding. DMF-Assisted Radical Cyclization of o-Isocyanodiaryl Ethers via 1,5-Aryl Migration: Construction of 2-Arylbenzoxazoles. The Journal of Organic Chemistry 2022, 87 (2) , 1485-1492. https://doi.org/10.1021/acs.joc.1c02806
  3. Jiapian Huang, Zhiyuan Chen, Jie Wu. Recent Progress in Methyl-Radical-Mediated Methylation or Demethylation Reactions. ACS Catalysis 2021, 11 (17) , 10713-10732. https://doi.org/10.1021/acscatal.1c02010
  4. Tao Cai, Fangqi Shen, Yuqi Ni, Huiting Xu, Runpu Shen, Yuzhen Gao. Cascade Radical Annulation of 2-Alkynylthio(seleno)anisoles with Acetone or Acetonitrile: Synthesis of 3-Acetomethyl- or Cyanomethyl-Substituted Benzothio(seleno)phenes. The Journal of Organic Chemistry 2021, 86 (1) , 1002-1011. https://doi.org/10.1021/acs.joc.0c02444
  5. Bagrat A. Shainyan, Larisa V. Zhilitskaya, Nina O. Yarosh. Synthetic Approaches to Biologically Active C-2-Substituted Benzothiazoles. Molecules 2022, 27 (8) , 2598. https://doi.org/10.3390/molecules27082598
  6. Xinjie Yang, Hao Wang, Yanhua Zhang, Weike Su, Jingbo Yu. Generation of aryl radicals from in situ activated homolytic scission: driving radical reactions by ball milling. Green Chemistry 2022, 2 https://doi.org/10.1039/D2GC00910B
  7. Feng Wu, Han Yao, Wei Li, Niuniu Zhang, Yangyang Fan, Albert S.C. Chan, Xingshu Li, Baijiao An. Synthesis and evaluation of novel 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibition agents. Bioorganic & Medicinal Chemistry Letters 2021, 48 , 128253. https://doi.org/10.1016/j.bmcl.2021.128253
  8. Xiao‐Yu Xie, Yang Li, Yun‐Tao Xia, Kai Luo, Lei Wu. Visible Light‐Induced Metal‐Free and Oxidant‐Free Radical Cyclization of (2‐Isocyanoaryl)(methyl)sulfanes with Ethers. European Journal of Organic Chemistry 2021, 2021 (30) , 4273-4277. https://doi.org/10.1002/ejoc.202100501
  9. T. Yadav, G. Brahmachari, I. Karmakar, P. Yadav, A.K. Prasad, A. Pathak, A. Agarwal, R. Kumar, V. Mukherjee, G.N. Pandey, R.R.F. Bento, N.P. Yadav. Conformational and vibrational spectroscopic investigation of N-n‑butyl, S-2-nitro-1-(p-tolyl)ethyl dithiocarbamate – a bio-relevant sulfur molecule. Journal of Molecular Structure 2021, 1238 , 130450. https://doi.org/10.1016/j.molstruc.2021.130450
  10. Jianhua Liao, Xiao Yang, Lu Ouyang, Yinlong Lai, Jiuzhong Huang, Renshi Luo. Recent advances in cascade radical cyclization of radical acceptors for the synthesis of carbo- and heterocycles. Organic Chemistry Frontiers 2021, 8 (6) , 1345-1363. https://doi.org/10.1039/D0QO01453B
  11. Yong-Jin Wu. Five-membered ring systems: with N and S atom. 2021,,, 325-344. https://doi.org/10.1016/B978-0-323-89812-6.00009-2
  12. Pei Xu, Yi-Ming Zhu, Xin-Yu Liu, Xiao-Zhou Zhou, Shun-Yi Wang, Shun-Jun Ji. Mn(III)-mediated radical reaction of 2-isocyano-6-alkenyl(alkynyl)benzonitriles with arylboronic acids: Synthesis of pyrroloisoquinoline derivatives. Chinese Chemical Letters 2021, 32 (1) , 413-416. https://doi.org/10.1016/j.cclet.2020.03.023
  13. Xue Sun, Teng Liu, Yan‐Tong Yang, Yue‐Jie Gu, Yu‐Wei Liu, Yi‐Gang Ji, Kai Luo, Jie Zhu, Lei Wu. Visible‐Light‐Promoted Regio‐ and Stereoselective Oxyalkenyl‐ation of Phosphinyl Allenes. Advanced Synthesis & Catalysis 2020, 362 (13) , 2701-2708. https://doi.org/10.1002/adsc.202000214
  14. Yue Liu, Yun‐Tao Xia, Su‐Hang Cui, Yi‐Gang Ji, Lei Wu. Palladium‐Catalyzed Cascade Hydrosilylation and Amino‐Methylation of Isatin Derivatives. Advanced Synthesis & Catalysis 2020, 362 (13) , 2632-2636. https://doi.org/10.1002/adsc.202000266

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