Advanced Search

Citation: Yang Wencheng, Qi Xiaoxu, Chen Pinhong, Liu Guosheng. Palladium-Catalyzed Intramolecular Fluoroarylation of Alkenes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 122-128. doi: 10.6023/cjoc201810026 shu

Palladium-Catalyzed Intramolecular Fluoroarylation of Alkenes

  • State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

  • Corresponding author: Chen Pinhong, pinhongchen@sioc.ac.cn Liu Guosheng, gliu@mail.sioc.ac.cn
  • Received Date: 20 October 2018
    Revised Date: 3 December 2018
    Available Online: 5 January 2018

    Fund Project: Project supported by he National Key R & D Program of China (973 Program, No. 2015CB856600), the National Natural Science Foundation of China (Nos. 21532009, 21672236, 21761142010, 21790330) and the Science Technology Commission of the Shanghai Municipality (Nos. 17QA1405200, 17JC1401200), and the Chinese Academy Sciences (Nos. XDB20000000, QYZDJSSW-SLH055) and the Youth Innovation Promotion Association (No.2018292)the Science Technology Commission of the Shanghai Municipality 17QA1405200the National Natural Science Foundation of China 21790330the National Natural Science Foundation of China 21532009the National Natural Science Foundation of China 21672236the Science Technology Commission of the Shanghai Municipality 17JC1401200the Chinese Academy Sciences QYZDJSSW-SLH055the Chinese Academy Sciences XDB20000000the Youth Innovation Promotion Association 2018292the National Natural Science Foundation of China 21761142010he National Key R & D Program of China (973 Program) 2015CB856600

Figures(3)

  • A novel palladium-catalyzed intramolecular fluoroarylation of alkenes has been developed, in which ArIF2 was employed as fluorine source as well as Ⅰ(Ⅲ) reagent to activate olefin, to deliver the fluoroarylation products from 4-aryl- 1-olefins in moderate to good yields. The current transformation presents a convenient method to provide fluorotetralins and fluorochromanes under mild conditions from alkenes tethered arenes.
  • 加载中
    1. [1]

      (a) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
      (b) Wang, J.; Sánchez-Rosellyó, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
      (c) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceña, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.

    2. [2]

      For reviews, see:
      (a) Cahard, D.; Xu, X.; Couve-Bonnaire, S.; Pannecoucke, X. Chem. Soc. Rev. 2010, 39, 558.
      (b) Grushin, V. V. Acc. Chem. Res. 2010, 43, 160.
      (c) Liu, G. Org. Biomol. Chem. 2012, 6243.
      (d) Wolstenhulme, J. R.; Gouverneur, V. Acc. Chem. Res. 2014, 47, 3560.
      (e) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.
      (f) Campbell, M. G.; Ritter, T. Chem. Rev. 2015, 115, 612.

    3. [3]

      For the selected examples on aminofluorination, see:
      (a) Wu. T.; Yin, G.; Liu, G. J. Am. Chem. Soc. 2009, 131, 16354.
      (b) Qiu, S.; Xu, T.; Zhou, J.; Guo, Y. Liu, G. J. Am. Chem. Soc. 2010, 132, 2856.
      (c) Kong, W.; Feige, P.; de Haro, T.; Nevado, C. Angew. Chem., Int. Ed. 2013, 52, 2469.
      (d) Li, Z.; Song, L.; Li, C. J. Am. Chem. Soc. 2013, 135, 4640.
      (e) Huang, H.-T.; Lacy, T. C.; Blachut, B.; Ortiz Jr, G. X.; Wang, Q. Org. Lett. 2013, 15, 1818.
      (f) Li, Z.; Zhang, C.; Zhu, L.; Liu, C.; Li, C. Org. Chem. Front. 2014, 1, 100.
      (g) Zhang, H.; Song, Y.; Zhao, J.; Zhang, J.; Zhang, Q. Angew. Chem., Int. Ed. 2014, 53, 11079.
      (h) Cui, J.; Jia, Q.; Feng, R.-Z.; Liu, S.-S.; He, T.; Zhang, C. Org. Lett. 2014, 16, 1442.
      (i) Lu, D.-F.; Liu, G.-S.; Zhu, C.-L.; Yuan, B.; Xu, H. Org. Lett. 2014, 16, 2912.
      (j) Yuan, W.; Szabo, K. J. Angew. Chem. Int. Ed. 2015, 54, 8533.
      (k) Lu, D.-F.; Zhu, C.-L.; Sears, J. D.; Xu, H. J. Am. Chem. Soc. 2016, 138, 11360.

    4. [4]

      For selected examples on oxyfluorination, see:
      (a) Wilkinson, S. C.; Lozano, O.; Schuler, M.; Pacheco, M. C.; Salmon, R.; Gouverneur, V. Angew. Chem., Int. Ed. 2009, 48, 7083.
      (b) Rauniyar, V.; Lackner, A. D.; Hamilton, G. L.; Toste, F. D. Science 2011, 334, 1681.
      (c) Peng, H.; Yuan, Z.; Wang, H.-Y., Guo, Y.-L.; Liu, G. Chem. Sci. 2013, 4, 3172.
      (d) Egami, H.; Asada, J.; Sato, K.; Hashizume, D.; Kawato, Y.; Hamashima, Y. J. Am. Chem. Soc. 2015, 137, 10132.
      (e) Geary, G. C.; Hope, E. G.; Stuart, A. M. Angew. Chem., Int. Ed. 2015, 54, 14911.

    5. [5]

      For selected examples on carbofluorination, see:
      (a) Cochrane, N. A.; Nguyen, H.; Gagne, M. R. J. Am. Chem. Soc. 2013, 135, 628.
      (b) Zhu, L.; Chen, H.; Wang Z.; Li, C. Org. Chem. Front. 2014, 1, 1299.
      (c) Wang, H.; Guo, L.-N.; Duan, X.-H. Chem. Commun. 2014, 50, 7382.
      (d) Liu, Z.; Chen, H.; Lv, Y.; Tan, X.; Shen, H.; Yu, H.-Z.; Li, C. J. Am. Chem. Soc. 2018, 140, 6169.

    6. [6]

      Other fluorination of alkenes, see:
      (a) Barker, T. J.; Boger, D. L. J. Am. Chem. Soc. 2012, 134, 13588.
      (b) Zhang, C.; Li, Z.; Zhu, L.; Yu, L.; Wang, Z.; Li, C. J. Am. Chem. Soc. 2013, 135, 14082.
      (c) Emer, E.; Pfeifer, L.; Brown, J. M.; Gouverneur, V. Angew. Chem., Int. Ed. 2014, 53, 4181.
      (d) Yuan, Z.; Wang, H.-Y.; Mu, X.; Chen, P.; Guo, Y.-L.; Liu, G. J. Am. Chem. Soc. 2015, 137, 2468.
      (e) Banik, S. M.; Medley, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2016, 138, 5000.
      (f) Molnár, I. G.; Gilmour, R. J. Am. Chem. Soc. 2016, 138, 5004.
      (g) Banik, S. M.; Medley, J. M.; Jacobsen, E. N. Science 2016, 353, 51.
      (h) Woerly, E. M.; Banik, S. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2016, 138, 13858.

    7. [7]

      (a) Talbot, E. P. A.; Fernandes, T. A.; McKenna, J. M.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 4101.
      (b) He, Y.; Yang, Z.; Thornbury, R. T.; Toste, F. D. J. Am. Chem. Soc. 2015, 137, 12207.
      (c) Miró, J.; de Pozo, C.; Toste, F. D.; Fustero, S. Angew. Chem., Int. Ed. 2016, 55, 9045.
      (d) Thornbury, R. T.; Saini, V.; Fernandes, T. A.; Santiago, C. B.; Talbot, E. P. A.; Sigman, M. S.; McKenna, J. M.; Toste, F. D. Chem. Sci. 2017, 8, 2890.

    8. [8]

      Tang, H.-J.; Lin, L.-Z.; Feng, C.; Loh, T.-P. Angew. Chem., Int. Ed. 2017, 56, 9872.  doi: 10.1002/anie.201705321

    9. [9]

      (a) Guo, R.; Yang, H.; Tang, P. Chem. Commun. 2015, 51, 8829.
      (b) Kindt, S.; Heinrich, M. R. Chem. Eur. J. 2014, 20, 15344.

    10. [10]

      Yin, G.; Mu, X.; Liu, G. Acc. Chem. Res. 2016, 49, 2413.  doi: 10.1021/acs.accounts.6b00328

    11. [11]

      (a) Li, M.; Yu, F.; Qi, X.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2016, 55, 13843.
      (b) Li, M.; Yu, F.; Chen, P.; Liu, G. J. Org. Chem. 2017, 82, 11682.
      (c) Qi, X.; Yu, F.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2017, 56, 12692.

    12. [12]

      (a) Taniguchi, K.; Nagano, M.; Hattori, K.; Tsubaki, K.; Okitsu, O.; Tabuchi, S. US 5763489, 1998.
      (b) Poirier, D. Anticancer Agents Med. Chem. 2009, 9, 642.

    13. [13]

      Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654.  doi: 10.1021/jacs.5b02244

    14. [14]

      (a) Kang, Y.-B.; Gade, L. H. J. Am. Chem. Soc. 2011, 133, 3658.
      (b) Izquierdo, S.; Essafi, S.; del Rosal, I.; Vidossich, P.; Pleixats, R.; Vallribera, A.; Ujaque, G.; Lledós, A.; Shafir, A. J. Am. Chem. Soc. 2016, 138, 12747.

    15. [15]

      Liu, R.; Lu, Z.-H.; Hu, X.-H.; Li, J.-L.; Yang, X.-J. Org. Lett. 2015, 17, 1489.  doi: 10.1021/acs.orglett.5b00376

    16. [16]

      (a) Qiu, S.; Xu, T.; Zhou, J.; Guo, Y.-L.; Liu, G. J. Am. Chem. Soc. 2010, 132, 2856.
      (b) Peng, H.; Yuan, Z.; Wang, H.-Y.; Guo, Y.-L.; Liu, G. Chem. Sci. 2013, 4, 3172.

    17. [17]

      Sharma, H.; Santra, S.; Debnath, J.; Antonio, T.; Reith, M.; Dutta, A. Bioorg. Med. Chem. 2014, 22, 311.

    18. [18]

      Choi, P. J.; Rathwell, D. C. K.; Brimble, M. A. Tetrahedron Lett. 2009, 50, 3245.  doi: 10.1016/j.tetlet.2009.02.030

    19. [19]

      Parrish, J. P.; Sudaresan, B.; Jung, K. W. Synth. Commun. 1999, 29, 4423.  doi: 10.1080/00397919908086606

    20. [20]

      Hanamoto, T.; Shindo, K.; Matsuoka, M.; Kiguchi, Y.; Kondo, M. J. Chem. Soc., Perkin Trans. 1 2000, 103.

  • 加载中
    1. [1]

      Yunqiang Li , Yongxian Huang , Sinuo Li , He Huang , Zhiwei Jiao . Elaborating azaaryl alkanes enabled by photoredox/palladium dual catalyzed dialkylation of azaaryl alkenes. Chinese Chemical Letters, 2025, 36(4): 110051-. doi: 10.1016/j.cclet.2024.110051

    2. [2]

      Junlong Tang , Yuhan Zhao , Yangbin Jin , Liren Zhang , Yuanfang Wang , Wanqing Wu , Huanfeng Jiang . Palladium-catalyzed modular biomimetic synthesis of lignans derivatives. Chinese Chemical Letters, 2025, 36(7): 110969-. doi: 10.1016/j.cclet.2025.110969

    3. [3]

      Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954

    4. [4]

      Jianyi Shi , Chengyi Peng , Jiali Qiu , Shuanglong Li , Wenyan Zhao , Xiang Sun , Shikai Xiang , Yandong Wu , Wenhan Xu , Fei Pan , Linxing Zhang , Fei Ye . Cobalt-catalyzed regiodivergent hydroalkenylation of alkenes. Chinese Chemical Letters, 2026, 37(9): 112824-. doi: 10.1016/j.cclet.2026.112824

    5. [5]

      Wenze Shi , Yang Dong , Xihong Wang , Min Wang , Jian Liao . SOP-ligand enabled palladium-catalyzed enantioselective anti-Markovnikov hydrothioesterification of α-substituted styrenes. Chinese Chemical Letters, 2025, 36(11): 111023-. doi: 10.1016/j.cclet.2025.111023

    6. [6]

      Tianzhu Qin , Weiwei Zi . Palladium-catalyzed enantioselective [2σ + 2π] cycloadditions of vinyl-carbonyl-bicyclo[1.1.0]butanes with arylidenemalononitriles. Chinese Chemical Letters, 2026, 37(1): 111072-. doi: 10.1016/j.cclet.2025.111072

    7. [7]

      Shihaozhi Wang , Jia-Hui Shi , Shan Xu , Xue-Jing Zhang , Ming Yan . Palladium-catalyzed carbene C-H insertion reaction of non-activated arenes. Chinese Chemical Letters, 2026, 37(4): 111225-. doi: 10.1016/j.cclet.2025.111225

    8. [8]

      Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495

    9. [9]

      Wenyan Zhao , Tiantian Liang , Dongcheng Zheng , Jiali Qiu , Juan Zheng , Yandong Wu , Wenhan Xu , Liang Liu , Fei Ye . Nickel-catalyzed quantitative deuterated reduction of quinolines and alkenes. Chinese Chemical Letters, 2026, 37(8): 112035-. doi: 10.1016/j.cclet.2025.112035

    10. [10]

      Jie Zhou , Luping Hu , Rui Wang , Ruijie Wang , Jun Xu , Huajian Xu . Three-component alkenylcarboxylation of two distinct alkenes with CO2 via photoinduced palladium catalysis. Chinese Chemical Letters, 2026, 37(4): 111304-. doi: 10.1016/j.cclet.2025.111304

    11. [11]

      Junqi Su , Wenhao Liu , Jianjun Wang , Weifen Luo , Yangyang Ma , Leiyang Lv , Zhiping Li . Palladium-catalyzed ring-opening defluorinative cross-coupling of gem-difluorocyclopropanes with fluoromalonates or fluorobis(phenylsulfonyl)methane. Chinese Chemical Letters, 2026, 37(3): 111288-. doi: 10.1016/j.cclet.2025.111288

    12. [12]

      Fan Chen , Xiaoyu Zhao , Weihang Miao , Yingying Li , Ye Yuan , Lingling Chu . Regio- and enantioselective hydrofluorination of internal alkenes via nickel-catalyzed hydrogen atom transfer. Chinese Chemical Letters, 2025, 36(5): 110239-. doi: 10.1016/j.cclet.2024.110239

    13. [13]

      Luyun Zhang , Ding Liu , Huri Piao , Zhenhua Jia , Fen-Er Chen . A modified Bis-OPNN phosphorus ligand for Rh-catalyzed linear-selective hydroformylation of alkenes. Chinese Chemical Letters, 2025, 36(7): 110640-. doi: 10.1016/j.cclet.2024.110640

    14. [14]

      Xin-Juan Wang , Yao-Hang Cheng , Xin-Yan Lv , Li-Ye Liang , Guang-Hui An , Guang-Ming Li . Ruthenium-catalyzed alkylarylation of alkenes via para-selective C-H functionalization of unprotected anilines. Chinese Chemical Letters, 2026, 37(8): 112154-. doi: 10.1016/j.cclet.2025.112154

    15. [15]

      Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157

    16. [16]

      Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688

    17. [17]

      Wei-Cheng Zhao , Yan He , Chen-Hui Jiang , Peng Liu , Qian Gao , Duo-Duo Hu , Xi-Sheng Wang . Asymmetric construction of non-activated C-SCF3 stereocenter via copper-catalyzed hydroallylation of SCF3-alkenes. Chinese Chemical Letters, 2026, 37(2): 111487-. doi: 10.1016/j.cclet.2025.111487

    18. [18]

      Er-Meng Wang , Ziyi Wang , Xu Ban , Xiaowei Zhao , Yanli Yin , Zhiyong Jiang . Chemoselective photocatalytic sulfenylamination of alkenes with sulfenamides via energy transfer. Chinese Chemical Letters, 2024, 35(12): 109843-. doi: 10.1016/j.cclet.2024.109843

    19. [19]

      Haibo Mei , Anas Semghouli , Loránd Kiss , Jianlin Han . Recent advances on cyclization reaction of indole-tethered alkenes for the construction of polyheterocycles. Chinese Chemical Letters, 2026, 37(8): 112405-. doi: 10.1016/j.cclet.2026.112405

    20. [20]

      Shuai Zhu , Mingjie Chen , Haichao Shen , Hanming Ding , Wenbo Li , Junliang Zhang . Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature. Chinese Chemical Letters, 2024, 35(11): 109879-. doi: 10.1016/j.cclet.2024.109879

Get Citation
PDF
XML
Metrics
  • PDF Downloads(12)
  • Abstract views(1912)
  • HTML views(209)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint