Citation: Tao Pingfang, Huang Jun, Liu Yuzhao, Wei Guangming, Wang Yifei, Wei Xiansheng, Huang Guobao, Li Xiuying. Palladium-Catalyzed Asymmetric Ring-Opening Reactions of Oxabenzonorbornadienes with Potassium Trifluoroborate Salts[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1630-1637. doi: 10.6023/cjoc201912030 shu

Palladium-Catalyzed Asymmetric Ring-Opening Reactions of Oxabenzonorbornadienes with Potassium Trifluoroborate Salts

  • Corresponding author: Huang Guobao, lzjx0915@163.com Li Xiuying, lxya8401@163.com
  • These authors contributed equally to this work.
  • Received Date: 22 December 2019
    Revised Date: 11 March 2020
    Available Online: 31 March 2020

    Fund Project: the Open Fund of Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology Research Grant KF04Project supported by the National Natural Science Foundation of China (No. 21961042), the Natural Science Foundation of Guangxi Province (No. 2018GXNSFAA294064) and the Open Fund of Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology Research Grant (No. KF04)the National Natural Science Foundation of China 21961042the Natural Science Foundation of Guangxi Province 2018GXNSFAA294064

Figures(2)

  • A new, versatile and highly efficient palladium-catalyzed asymmetric ring-opening reaction of oxabenzonor-bornadienes with a wide range of potassium trifluoroborate salts was developed. The corresponding cis-2-aryl-1, 2-dihydronaphthalen-1-ol products were obtained in good yields with moderate to good enantioselectivities under mild conditions.
  • 加载中
    1. [1]

      (a) Roberto, P.; Francesco, B.; Nicola, C. A.; Marcello, L.; Vincenzo, T.; Francesco, F.; Vincenzo, O.; Alberto, G.; Stefano, G. J. Med. Chem. 1995, 38, 942.
      (b) Scott, E. S.; Felix, A. A.; Ratna, C.; David, E. N.; Val, J. W.; Richard, B. M. J. Med. Chem. 1995, 38, 2395.
      (c) Lautens, M.; Rovis, T. J. Org. Chem. 1997, 62, 5246.
      (d) Lautens, M.; Rovis, T. J. Am. Chem. Soc. 1997, 119, 11090.
      (e) Lautens, M.; Fagnou, K.; Taylor, M.; Rovis, T. J. Organomet. Chem. 2001, 624, 259.
      (f) Lautens, M.; Fagnou, K.; Zunic, V. Org. Lett. 2002, 4, 3465.
      (g) Tsoung, J.; Krämer, K.; Zajdlik, A.; Liébert, C.; Lautens, M. J. Org. Chem. 2011, 76, 9031.

    2. [2]

      For reviews, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
      (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
      (c) Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.
      (d) Rayabarapu, D. K.; Cheng, C.-H. Acc. Chem. Res. 2007, 40, 971.

    3. [3]

      Nakamura, M.; Matsuo, K.; Inoue, T.; Nakamura, E. Org. Lett. 2003, 5, 1373.  doi: 10.1021/ol034375b

    4. [4]

      (a) Lautens, M.; Ma, S. J. Org. Chem. 1996, 61, 7246.
      (b) Rayabarapu, D. K.; Chiou, C.-F.; Cheng, C.-H. Org. Lett. 2002, 4, 1679.
      (c) Wang, G.; Gan, Y.; Liu, Y. Chin. J. Chem. 2018, 36, 916.
      (d) Fu, X.-P.; Xiao, Y.-L.; Zhang, X. Chin. J. Chem. 2018, 36, 143.

    5. [5]

      (a) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703.
      (b) Zhang, W.; Wang, L.-X.; Shi, W.-J.; Zhou, Q.-L. J. Org. Chem. 2005, 70, 3734.
      (c) Zhang, L.-Y.; Wang, L. Chin. J. Chem. 2006, 24, 1605.

    6. [6]

      (a) Carreras, J.; Avenoza, A.; Busto, J. H.; Peregrina, J. M. Org. Lett. 2007, 9, 1235.
      (b) Cortez, G. A.; Baxter, C. A.; Schrock, R. R.; Hoveyda, A. H. Org. Lett. 2007, 9, 2871.
      (c) Machin, B. P.; Howell, J.; Mandel, J.; Blanchard, N.; Tam, W. Org. Lett. 2009, 11, 2077.

    7. [7]

      (a) Lautens, M.; Fagnou, K.; Taylor, M. Org. Lett. 2000, 2, 1677.
      (b) Lautens, M.; Fagnou, K. Tetrahedron 2001, 57, 5067.
      (c) Lautens, M.; Fagnou, K. J. Am. Chem. Soc. 2001, 123, 7170.
      (d) Preetz, A.; Kohrt, C.; Drexler, H. J.; Torrens, A.; Buschmann, H.; Lopez, M. G.; Heller, D. Adv. Synth. Catal. 2010, 352, 2073.

    8. [8]

      (a) Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804.
      (b) Li, L.-P.; Rayabarapu, D. K.; Nandi, M.; Cheng, C.-H. Org. Lett. 2003, 5, 1621.
      (c) Cabrera, S.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2004, 43, 3944.
      (d) Ogura, T.; Yoshida, K.; Yanagisawa, A.; Imamoto, T. Org. Lett. 2009, 11, 2245.
      (e) Li, M.; Yan, X.-X.; Hong, W.; Zhu, X.-Z.; Cao, B.-X.; Sun, J.; Hou, X.-L. Org. Lett. 2004, 6, 2833.

    9. [9]

      (a) Pan, X.-J.; Huang, G.-B.; Long, Y.-H.; Zuo, X.-J.; Xu, X.; Gu, F.-L.; Yang, D.-Q. J. Org. Chem. 2014, 79, 187.
      (b) Yang, D.-Q.; Liang, N. Org. Biomol. Chem. 2014, 12, 2080.
      (c) Meng, L.; Yang, W.; Pan, X.-J.; Tao, M.; Cheng, G.; Wang, S.-Y.; Zeng, H.-P.; Long, Y.-H.; Yang, D.-Q. J. Org. Chem. 2015, 80, 2503.

    10. [10]

      (a) Yang, D.-Q.; Long, Y.-H.; Wang, H.; Zhang, Z.-M. Org. Lett. 2008, 10, 4723.
      (b) Long, Y.-H.; Yang, D.-Q.; Zhang, Z.-M.; Wu, Y.-J.; Zeng, H.-P.; Chen, Y. J. Org. Chem. 2010, 75, 7291.
      (c) Yang, D.-Q.; Long, Y.-H.; Zhang, J.-F.; Zeng, H.-P.; Wang, S.-Y.; Li, C.-R. Organometallics 2010, 29, 3477.
      (d) Yang, D.-Q.; Long, Y.-H.; Wu, Y.-J.; Zuo, X.-J.; Tu, Q.-Q.; Fang, S.; Jiang, L.-S.; Wang, S.-Y.; Li, C.-R. Organometallics 2010, 29, 5936.
      (e) Fang, S.; Liang, X.-L.; Long, Y.-H.; Li, X.-L.; Yang, D.-Q.; Wang, S.-Y.; Li, C.-R. Organometallics 2012, 31, 3113.
      (f) Cheng, H.-C.; Yang, D.-Q. J. Org. Chem. 2012, 77, 9756.
      (g) Yang, D.-Q.; Xia, J.-Y.; Long, Y.-H.; Zeng, Z.-Y.; Zuo, X.-J.; Wang, S.-Y.; Li, C.-R. Org. Biomol. Chem. 2013, 11, 4871.
      (h) Yang, W.; Luo, R.-S.; Yang, D.-Q. Molecules 2015, 20, 21103.

    11. [11]

      (a) Feng, C.-C.; Nandi, M.; Sambaiah, T.; Cheng, C.-H. J. Org. Chem. 1999, 64, 3538.
      (b) Chen, C.-L.; Martin, S. F. Org. Lett. 2004, 6, 3581.
      (c) Chen, C.-L.; Martin, S.-F. J. Org. Chem. 2006, 71, 4810.

    12. [12]

      (a) Arrayas, R. G.; Cabrera, S.; Carretero, J. C. Org. Lett. 2003, 5, 1333.
      (b) Zhang, W.; Zhu, S.-F.; Qiao, X.-C.; Zhou, Q.-L. Chem.-Asian J. 2008, 3, 2105.

    13. [13]

      (a) Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311.
      (b) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390.
      (c) Lautens, M.; Dockendorff, C. Org. Lett. 2003, 5, 3695.
      (d) Zhang, T.-K.; Mo, D.-L.; Dai, L.-X.; Hou, X.-L. Org. Lett. 2008, 10, 3689.
      (d) Luo, F.; Pan, C.; Cheng, J. Chin. J. Org. Chem. 2010, 30, 633.

    14. [14]

      (a) Li, Y.; Yang, W.; Cheng, G.; Yang, D.-Q. J. Org. Chem. 2016, 81, 4744.
      (b) Wu, R. H.; Yang, W.; Chen, W. K.; Yang, D.-Q. Org. Chem. Front. 2017, 4, 1921.
      (c) Zhang, S.; Yang, S.; Huang, L.; Zhao, B.; Cheng, K.; Qi, C. Chin. J. Org. Chem. 2015, 35, 2259 (in Chinese).
      (张诗浓, 杨胜虎, 黄乐浩, 赵保丽, 程凯, 齐陈泽, 有机化学, 2015, 35, 2259.)

    15. [15]

      (a) Seigerman, C. K.; Micyus, T. M.; Neufeldt, S. R.; Sanford, M. S. Tetrahedron 2013, 69, 5580.
      (b) Dubbaka, S. R.; Narreddula, V. R.; Gadde, S.; Mathew, T. Tetrahedron 2014, 70, 9676.

    16. [16]

      Molander, G. A.; Sandrock, D. L. Curr. Opin. Drug Discovery Dev. 2009, 12, 811.

    17. [17]

      (a) Li, S. F.; Xu, J. B.; Fan, B.-M.; Lu, Z. W.; Zeng, C. Y.; Bian, Z. X.; Zhou, Y. Y.; Wang, J. Chem.-Eur. J. 2015, 21, 9003.
      (b) Xu, X.; Chen, J.-C.; He, Z.-X.; Zhou, Y.-Y.; Fan, B.-M. Org. Biomol. Chem. 2016, 14, 2480.

    18. [18]

      (a) Barbeiro, C. S.; Vasconcelos, S. N. S.; de Oliveira, I. M.; Zukerman-Schpector, J.; Caracelli, I.; Maganhi, S. H.; Stefani, H. A. ChemistrySelect 2017, 2, 8173.
      (b) Liu, L.; Dong, Y.; Pang, B.; Ma, J. J. Org. Chem. 2014, 79, 7193.

    19. [19]

      Zhang, W.; Chen, J. C.; Zeng, G. Z.; Yang, F.; Xu, J. B.; Sun, W. Q.; Shinde, M. V.; Fan, B. M. J. Org. Chem. 2017, 82, 2641.  doi: 10.1021/acs.joc.6b03038

    20. [20]

      (a) Lautens, M.; Fagnou, K.; Yang, D.-Q. J. Am. Chem. Soc. 2003, 125, 14884.
      (b) Villeneuve, K.; Tam, W. Organometallics 2007, 26, 6082.

  • 加载中
    1. [1]

      Yue SunLiming YangYaohang ChengGuanghui AnGuangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250

    2. [2]

      Rong-Nan YiWei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787

    3. [3]

      Feng ZhaoHongyu DingTing SunChao ShenZu-Li WangWei WeiDong Yi . Visible-light-promoted multi-component carbene transfer reactions of diazo compounds via ring-opening of cyclic ethers. Chinese Chemical Letters, 2026, 37(2): 111834-. doi: 10.1016/j.cclet.2025.111834

    4. [4]

      Junqi SuWenhao LiuJianjun WangWeifen LuoYangyang MaLeiyang LvZhiping 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

    5. [5]

      Rong-Nan YiJun JiangWei-Min He . Pd/NHC-catalyzed ring-opening cross-coupling of gem-difluorocyclopropanes via a 3,3′-reductive elimination pathway. Chinese Chemical Letters, 2026, 37(4): 112163-. doi: 10.1016/j.cclet.2025.112163

    6. [6]

      Qinghong ZhangQiao ZhaoXiaodi WuLi WangKairui ShenYuchen HuaCheng GaoYu ZhangMei PengKai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167

    7. [7]

      Xue DuZe-Hua SunPenglei ZhangLi-Ping XuXiaodong Xiong . Asymmetric chloro– and selenocyclization of 2-alkenyl anilides enabled by tertiary ammonium salt catalysis. Chinese Chemical Letters, 2026, 37(4): 111259-. doi: 10.1016/j.cclet.2025.111259

    8. [8]

      Peng WangGuanyu ZhaoYicai PanYujing LiChenxi FuShipeng SunJunqi GaiJinping MuXue BaiXiaohui LiJinfeng SunXiaodong ShiRui He . Dual-salt electrolyte strategy enables stable interface reaction and high-performance lithium-ion batteries at low temperature. Chinese Chemical Letters, 2025, 36(11): 111190-. doi: 10.1016/j.cclet.2025.111190

    9. [9]

      Zhuojun DuanPeiyue JinHouying XingJian ChenYueting YangYawen TanSong Liu . Salt-assisted synthesis of WTe2 contact electrodes for efficient MoS2-based hydrogen evolution reaction. Chinese Chemical Letters, 2026, 37(2): 111917-. doi: 10.1016/j.cclet.2025.111917

    10. [10]

      Wen-Rui LiRu-Bing WangHuiqiang WangJin-Yao YongYu-Huan LiShi-Shan YuShuang-Gang Ma . Ring-reorganization strategy for asymmetric synthesis of sesquiterpenoid illihenin A and its antiviral activity evaluation. Chinese Chemical Letters, 2025, 36(11): 110945-. doi: 10.1016/j.cclet.2025.110945

    11. [11]

      Yuhao ZhouSiyuan WuXiaozhe RenHongjin LiShu LiTianying Yan . Effects of salt fraction on the Na+ transport in salt-in-ionic liquid electrolytes. Chinese Chemical Letters, 2025, 36(6): 110048-. doi: 10.1016/j.cclet.2024.110048

    12. [12]

      Qiangwei WangHuijiao LiuMengjie WangHaojie ZhangJianda XieXuanwei HuShiming ZhouWeitai Wu . Observation of high ionic conductivity of polyelectrolyte microgels in salt-free solutions. Chinese Chemical Letters, 2024, 35(4): 108743-. doi: 10.1016/j.cclet.2023.108743

    13. [13]

      Kailong ZhangChao ZhangLuanhui WuQidong YangJiadong ZhangGuang HuLiang SongGaoran LiWenlong Cai . Chloride molten salt derived attapulgite with ground-breaking electrochemical performance. Chinese Chemical Letters, 2024, 35(10): 109618-. doi: 10.1016/j.cclet.2024.109618

    14. [14]

      Peiyan ZhuYanyan YangHui LiJinhua WangShiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533

    15. [15]

      Zhen LiuZhi-Yuan RenChen YangXiangyi ShaoLi ChenXin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939

    16. [16]

      Yu-Hang MiaoZheng-Xu ZhangXu-Yi HuangYuan-Zhao HuaShi-Kun JiaXiao XiaoMin-Can WangLi-Ping XuGuang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830

    17. [17]

      Jieshuai XiaoYuan ZhengYue ZhaoZhuangzhi ShiMinyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243

    18. [18]

      Fangqing ZhangYu WangZhenda TanYangbin LiuLijuan SongXiaoming Feng . Catalytic asymmetric inverse-electron-demand Diels–Alder reaction of 2-pyrones with aryl enol ethers. Chinese Chemical Letters, 2025, 36(7): 110581-. doi: 10.1016/j.cclet.2024.110581

    19. [19]

      Yi-Kao XuGuo-Ping LuoLiang-Bin HuWei-Min He . Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes. Chinese Chemical Letters, 2025, 36(8): 111226-. doi: 10.1016/j.cclet.2025.111226

    20. [20]

      Junhan LuoQi QingLiqin HuangZhe WangShuang LiuJing ChenYuexiang Lu . Non-contact gaseous microplasma electrode as anode for electrodeposition of metal and metal alloy in molten salt. Chinese Chemical Letters, 2024, 35(4): 108483-. doi: 10.1016/j.cclet.2023.108483

Metrics
  • PDF Downloads(8)
  • Abstract views(1221)
  • HTML views(177)

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
Return