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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-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
10. [10]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan 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
11. [11]
  Junhan Luo , Qi Qing , Liqin Huang , Zhe Wang , Shuang Liu , Jing Chen , Yuexiang 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
12. [12]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
13. [13]
  Jiao Wang , Shuang-Yan Lang , Zhen-Zhen Shen , Gui-Xian Liu , Jian-Xin Tian , Yuan Li , Rui-Zhi Liu , Rui Wen . In situ imaging of the interfacial processes manipulated by salt concentration on zinc anodes in zinc metal batteries. Chinese Chemical Letters, 2025, 36(4): 109815-. doi: 10.1016/j.cclet.2024.109815
14. [14]
  Mao-Fan Li , Ming‐Yu Guo , De-Xuan Liu , Xiao-Xian Chen , Wei-Jian Xu , Wei-Xiong Zhang . Multi-stimuli responsive behaviors in a new chiral hybrid nitroprusside salt (R-3-hydroxypyrrolidinium)₂[Fe(CN)₅(NO)]. Chinese Chemical Letters, 2024, 35(12): 109507-. doi: 10.1016/j.cclet.2024.109507
15. [15]
  Ningning Gao , Yue Zhang , Zhenhao Yang , Lijing Xu , Kongyin Zhao , Qingping Xin , Junkui Gao , Junjun Shi , Jin Zhong , Huiguo Wang . Ba²⁺/Ca²⁺ co-crosslinked alginate hydrogel filtration membrane with high strength, high flux and stability for dye/salt separation. Chinese Chemical Letters, 2024, 35(5): 108820-. doi: 10.1016/j.cclet.2023.108820
16. [16]
  Hong Chen , Mao-Yin Ran , Long-Hua Li , Xin-Tao Wu , Hua Lin . [Cs14Cl][Tm71Se110]: An unusual salt-inclusion chalcogenide containing different valent Tm centers and ultralow thermal conductivity. Chinese Journal of Structural Chemistry, 2024, 43(10): 100397-100397. doi: 10.1016/j.cjsc.2024.100397
17. [17]
  Zhenzhen Zhao , Meichen Jiao , Jiejie Ling , Han Jiang , Yan Gao , Hao Xu , Hai-Qing Li , Jingang Jiang , Peng Wu , Le Xu . Toward the microporous zeolite family with tunable large-medium cage and pore opening. Chinese Journal of Structural Chemistry, 2024, 43(9): 100336-100336. doi: 10.1016/j.cjsc.2024.100336
18. [18]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
19. [19]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
20. [20]
  Yanxin Jiang , Kwai Wun Cheng , Zhiping Yang , Jun (Joelle) Wang . Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes. Chinese Chemical Letters, 2025, 36(5): 110231-. doi: 10.1016/j.cclet.2024.110231

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(720)
HTML views(119)

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