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

Tao Pingfang ^a,† ,
Huang Jun ^a,b,† ,
Liu Yuzhao ^a ,
Wei Guangming ^a ,
Wang Yifei ^a ,
Wei Xiansheng ^a ,
Huang Guobao ^a,, ,
Li Xiuying ^a,,

a.
Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science, Yulin Normal University, Yulin, Guangxi 537000
b.
College of Chemistry and Materials, Nanning Normal University, Nanning 530001

Corresponding author: Huang Guobao, lzjx0915@163.com Li Xiuying, lxya8401@163.com

^†

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.
- oxabenzonorbornadiene,
- trifluoroborate salt,
- asymmetric ring-opening reaction
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.
1. [1]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming 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 Yi , Wei-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]
  Hong Xin , Shutao Wang , Li-Na Guo , Cheng Guan , Jinyi Liao , Zi-Hang Yuan , Zhengze Zhang , Xin-Hua Duan . An unusual carbon radical-mediated ring-opening/amination or esterification cascade of unstrained α-haloalkyl cycloketone derivatives. Chinese Chemical Letters, 2026, 37(7): 111939-. doi: 10.1016/j.cclet.2025.111939
4. [4]
  Quanbin Jiang , Hui Jiao , Long Jiang , Xiaodan Zhao . A catalytic thiolation/dethiolation strategy for the ring-opening of cyclopropenes to access α,β-unsaturated nitriles and carbonyl compounds. Chinese Chemical Letters, 2026, 37(11): 112354-. doi: 10.1016/j.cclet.2025.112354
5. [5]
  Feng Zhao , Hongyu Ding , Ting Sun , Chao Shen , Zu-Li Wang , Wei Wei , Dong 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
6. [6]
  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
7. [7]
  Rong-Nan Yi , Jun Jiang , Wei-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
8. [8]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai 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
9. [9]
  Xue Du , Ze-Hua Sun , Penglei Zhang , Li-Ping Xu , Xiaodong 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
10. [10]
  Wenjing Dai , Xiaohui Zhang , Zhen Yin . Acid‑humidification strategy for suppressing salt formation to enhance the CO2 reduction reaction stability. Chinese Journal of Structural Chemistry, 2026, 45(5): 100888-100888. doi: 10.1016/j.cjsc.2026.100888
11. [11]
  Peng Wang , Guanyu Zhao , Yicai Pan , Yujing Li , Chenxi Fu , Shipeng Sun , Junqi Gai , Jinping Mu , Xue Bai , Xiaohui Li , Jinfeng Sun , Xiaodong Shi , Rui 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
12. [12]
  Zhuojun Duan , Peiyue Jin , Houying Xing , Jian Chen , Yueting Yang , Yawen Tan , Song 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
13. [13]
  Yuexia LI , Guodi CHEN , Jiani HE , Caiting JI , Yan SUN , Zhiyi ZHANG , Jianhuang ZENG . Oxygen reduction reaction performance and formation process mechanism on Pt_xCu₁ 3D nanoporous conductive networks via tuned inorganic salt self-assembly. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2203-2216. doi: 10.11862/CJIC.20260108
14. [14]
  Wen-Rui Li , Ru-Bing Wang , Huiqiang Wang , Jin-Yao Yong , Yu-Huan Li , Shi-Shan Yu , Shuang-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
15. [15]
  Yuhao Zhou , Siyuan Wu , Xiaozhe Ren , Hongjin Li , Shu Li , Tianying 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
16. [16]
  Dawei Li , Haoming Song , Yibo Shi , Guangliu Ran , Cuifen Zhang , Andong Zhang , Ya-Nan Chen , Gendi Zhang , Zaifei Ma , Wenkai Zhang , Cuihong Li , Yahui Liu , Hao Lu , Zhishan Bo . High-performance organic solar cells based on non-fused-ring electron acceptors bearing asymmetric fluorinated lateral substituents. Chinese Chemical Letters, 2026, 37(11): 112438-. doi: 10.1016/j.cclet.2026.112438
17. [17]
  Qiangwei Wang , Huijiao Liu , Mengjie Wang , Haojie Zhang , Jianda Xie , Xuanwei Hu , Shiming Zhou , Weitai 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
18. [18]
  Kailong Zhang , Chao Zhang , Luanhui Wu , Qidong Yang , Jiadong Zhang , Guang Hu , Liang Song , Gaoran Li , Wenlong 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
19. [19]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing 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
20. [20]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin 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

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(1666)
HTML views(238)

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