Palladium-Catalyzed Intramolecular Fluoroarylation of Alkenes

doi:10.6023/cjoc201810026

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 122-128.DOI: 10.6023/cjoc201810026 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Articles

钯催化烯烃的分子内氟芳基化反应

杨文铖, 亓晓旭, 陈品红, 刘国生

中国科学院上海有机化学研究所金属有机化学国家重点实验室分子合成科学卓越创新中心上海 200032

收稿日期:2018-10-20 修回日期:2018-12-03 发布日期:2018-12-05
通讯作者: 陈品红, 刘国生 E-mail:pinhongchen@sioc.ac.cn;gliu@mail.sioc.ac.cn
基金资助:
国家重点基础研究发展计划（973计划，No.2015CB856600）、国家自然科学基金（Nos.21532009，21672236，21761142010，21790330）、上海市科学技术委员会（Nos.17QA1405200和17JC1401200）、中国科学院（Nos.XDB20000000，QYZDJSSW-SLH055）和青年创新促进会（No.2018292）资助项目.

Palladium-Catalyzed Intramolecular Fluoroarylation of Alkenes

Yang Wencheng, Qi Xiaoxu, Chen Pinhong, Liu Guosheng

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

Received:2018-10-20 Revised:2018-12-03 Published:2018-12-05
Contact: 10.6023/cjoc201810026 E-mail:pinhongchen@sioc.ac.cn;gliu@mail.sioc.ac.cn
Supported by:
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).

1. Palladium-Catalyzed Intramolecular Fluoroarylation of Alkenes.PDF(874KB)

Abstract

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.

Key words: palladium-catalyzed, alkenes, fluoroarylation, tetralin

Cite this article

Yang Wencheng, Qi Xiaoxu, Chen Pinhong, Liu Guosheng. Palladium-Catalyzed Intramolecular Fluoroarylation of Alkenes[J]. Chin. J. Org. Chem., 2019, 39(1): 122-128.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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] 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] 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] 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] 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] 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] (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] Tang, H.-J.; Lin, L.-Z.; Feng, C.; Loh, T.-P. Angew. Chem., Int. Ed. 2017, 56, 9872.
[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] Yin, G.; Mu, X.; Liu, G. Acc. Chem. Res. 2016, 49, 2413.
[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] (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] Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654.
[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] Liu, R.; Lu, Z.-H.; Hu, X.-H.; Li, J.-L.; Yang, X.-J. Org. Lett. 2015, 17, 1489.
[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] Sharma, H.; Santra, S.; Debnath, J.; Antonio, T.; Reith, M.; Dutta, A. Bioorg. Med. Chem. 2014, 22, 311.
[18] Choi, P. J.; Rathwell, D. C. K.; Brimble, M. A. Tetrahedron Lett. 2009, 50, 3245.
[19] Parrish, J. P.; Sudaresan, B.; Jung, K. W. Synth. Commun. 1999, 29, 4423.
[20] Hanamoto,T.; Shindo, K.; Matsuoka, M.; Kiguchi, Y.; Kondo, M. J. Chem. Soc., Perkin Trans. 1 2000, 103.

钯催化烯烃的分子内氟芳基化反应

Palladium-Catalyzed Intramolecular Fluoroarylation of Alkenes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Sida Li, Xing-Zhong Shu, Lipeng Wu. Zirconium and Titanium Mediated Hydroboration of Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1751-1760.
[2]	Jiajie Zhu, Yi Wan, Qiyang Yuan, Jinlian Wei, Yongqiang Zhang. Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3623-3634.
[3]	Yan Huang, Qian Zhang, Lewu Zhan, Jing Hou, Bindong Li. Hydrocarboxylation of Alkenes with Formate Salts via Photocatalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2568-2573.
[4]	Yazhou Wang, Yuhang Zhu, Lixia Xu, Rui He, Jian Zhang. Recent Advances in Geminal-Group-Directed Alkenyl C—H Functionalization [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2000-2014.
[5]	Duoduo Xiao, Hailing Liu, Peng Zhou, Jiantao Zhang, Weibing Liu. I₂/t-Butylhydroperoxide (TBHP)-Mediated Oxo-amidation of Alkenes with N,N-Dimethylformamide: A Facile Access to Aryl-α-ketoamide Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1438-1442.
[6]	Lüyin Zheng, Yihan Wang, Liuhuan Cai, Wei Guo. Progress in C—CF₃/C—N Bond Formation Reactions of Alkenes Involving in Free Radicals [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4078-4098.
[7]	Xiuying Li, Pingfang Tao, Yongyu Cheng, Qiong Hu, Weijuan Huang, Yun Li, Zhihui Luo, Guobao Huang. Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4169-4201.
[8]	Junfei Li, Yuling Han, Yanhong Liu, Jianxin Chen. Synthesis of β-Nitroamide Derivatives Based on Carbamoylsilane [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3880-3889.
[9]	Haorui Wang, Mengchun Ye. Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3152-3166.
[10]	Yuanyuan Ping, Haixia Song, Wangqing Kong. Recent Advances in Ni-Catalyzed Asymmetric Reductive Difunctionalization of Alkenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3302-3321.
[11]	Yang Han, Weichao Jiang, Jing Zhang, Jinsong Peng, Chunxia Chen. Visible-Light-Promoted Palladium-Catalyzed C—H Amination for the Synthesis of Carbazolequinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 266-276.
[12]	Yunshuai Huang, Xiaohui Jin, Fenglian Zhang, Yifeng Wang. 4-Dimethylaminopyridine-Boryl Radical Promoted Regioselective Radical Hydroboration of Electron-Deficient Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1957-1967.
[13]	Honglei Jin, Fengxuan Jiang, Kai Cheng, Lehao Huang. Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides and Its Application to the Synthesis of the Core Sturctures of Aporphine and Aristolactam Alkaloids [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1691-1702.
[14]	Lingling Zhang, Zhi Wang, Jian Wu, Xiaoqing Li. Synthesis of Nitro-Functionalized Isoquinolinediones via NaNO₂/Na₂S₂O₈-Mediated Arylnitration of Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1734-1738.
[15]	Xin Xi, Gongping Zhang, Jiancheng Li, Yanting Huang, Wenjun Jiang, Peng Wu, Hongping Zhu. Synthesis of Alkynes Composed of the Novel Substituents and Their Reactions with B(C₆F₅)₃ [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 766-775.