Nickel-Catalyzed Regioselective Coupling Reaction of 3,3,3-Trifluoropropene with Arylzinc Reagents

doi:10.6023/cjoc202005082

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3307-3313.DOI: 10.6023/cjoc202005082 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

镍催化下3,3,3-三氟丙烯与芳基锌试剂的区域选择性偶联反应

程然, 徐畅, 张新刚

中国科学院上海有机化学研究所分子合成卓越中心中国科学院有机氟化学重点实验室中国科学院大学上海 200032

收稿日期:2020-05-29 修回日期:2020-06-17 发布日期:2020-07-23
通讯作者: 张新刚 E-mail:xgzhang@mail.sioc.ac.cn
基金资助:
国家自然科学基金（Nos.21931013，21672238，21421002）和中国科学院先导专项（No.XDB20000000）资助项目.

Nickel-Catalyzed Regioselective Coupling Reaction of 3,3,3-Trifluoropropene with Arylzinc Reagents

Cheng Ran, Xu Chang, Zhang Xingang

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

Received:2020-05-29 Revised:2020-06-17 Published:2020-07-23
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21931013, 21672238, 21421002), and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000).

1. cjoc202005082.pdf(3110KB)

Abstract

3,3,3-Trifluoropropene (TFP) is an inexpensive and bulk industrial material and has important applications in the production of fluorinated polymers, refrigerant and so on. The use of TFP as a fluorine source enables access to a variety of fluorinated compounds. To date, important progress has been made in the transformations of TFP, however, most of the developed methods focused on the functionalization of carbon-carbon double bond of TFP. The controllable formation of fluorinated products via regio-selective functionalization of TFP received less attention. Herein, a nickel-catalyzed regioselective coupling of TFP with arylzinc reagents is described. By fine-tuning the reaction solvent, two different types of fluorinated products, gem-difluoroalkenes and Heck-type aryl-substituted TFPs, were obtained. The use of dioxane as the solvent led to a series of gem-difluoroalkenes in moderate to good yields with high regio-selectivity and functional group tolerance under mild reaction conditions. While, switching solvent from dioxane to N,N-dimethylformamide (DMF), the Heck-type aryl-substituted TFPs were obtained. This regioselective coupling provides an efficient route for applications of TFP in organic synthesis.

Key words: 3,3,3-trifluoropropene, nickel catalysis, arylzinc reagents, cross-coupling

Cite this article

Cheng Ran, Xu Chang, Zhang Xingang. Nickel-Catalyzed Regioselective Coupling Reaction of 3,3,3-Trifluoropropene with Arylzinc Reagents[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3307-3313.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, 2nd ed., Wiley-VCH, Weinheim, 2013.
(b) Groult, H.; Leroux, F. R.; Tressaud, A. Modern Synthesis Processes and Reactivity of Fluorinated Compounds, Elsevier, Amsterdam, 2017.
(c) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[2] (a) Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(c) O' Hagan, D. Chem. Soc. Rev. 2008, 37, 308.
(c) Zhang, F.-G.; Peng, X.; Ma, J.-A. Chin. J. Org. Chem. 2019, 39, 109(in Chinese). (张发光, 彭星, 马军安, 有机化学, 2019, 39, 109.)
(d) Huang, H.; Wang, X.; Wang, J.-B. Chin. J. Org. Chem. 2019, 39, 1(in Chinese). (黄航, 王兮, 王剑波, 有机化学, 2019, 39, 1.)
(e) Zhang, P.-P.; Lu, L.; Shen, Q.-L. Acta Chim. Sinica 2017, 75, 744(in Chinese). (张盼盼, 吕龙, 沈其龙, 化学学报, 2017, 75, 744.)
(f) Yang, Y.; You, Z.; Qing, F.-L. Acta Chim. Sinica 2012, 70, 2323(in Chinese). (杨义, 游正伟, 卿凤翎, 化学学报, 2012, 70, 2323.)
[3] (a) Feng, Z.; Xiao, Y.-L.; Zhan,g X.-G. Acc. Chem. Res. 2018, 51, 2264.
(b) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.
(c) Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328,1679.
(d) An, L.; Tong, F.-F.; Zhang, X.-G. Acta Chim. Sinica 2018, 76, 977(in Chinese). (安伦, 童非非, 张新刚, 化学学报, 2018, 76, 977.)
(e) Gao, X.; He, X.; Zhang, X.-G. Chin. J. Org. Chem. 2019, 39, 215(in Chinese).
(f) Xiao, Y.-L.; Pan, Q.; Zhang, X.-G. Acta Chim. Sinica 2015, 73, 383(in Chinese). (肖玉兰, 潘强, 张新刚, 化学学报, 2015, 73, 383.)
[4] (a) Kirsch, P. Modern Fluoroorganic Chemistry, 2nd ed., Wiley-VCH Verlag GmbH. & KGaA., Weinheim, 2013.
(b) Zhang, H. Organo-Fluorine Industry 2003, (3), 20(in Chinese). (张亨, 有机氟工业, 2003, (3), 20.)
[5] (a) Zhang, H.; Song, X. Z. Organo-Fluorine Industry 2007, 21(in Chinese). (张恒, 宋学章, 有机氟工业, 2007, (4), 21.)
(b) Brown, D. W.; Wall, L. A. J. Polym. Sci., Part A:Polym. Chem.1968, 6, 1367.
(c) Souzy, R.; Ameduri, B.; Boutevin, B. Prog. Polym. Sci. 2004, 29, 75.
(d) Gil, B.; Kasperski, J. Energies 2018, 11, 2136.
(e) Sha, M.; Xing, P.; Jiang, B. Chin. Chem. Lett. 2015, 26, 491.
(f) Gray, K. C.; Heider, P.; McGough, P.; Ondari, M.; Devaraj, J.; Yang, Q.; Frycek, G.; Graham, B.; Neuman, J.; Lorsbach, B. A.; Zhang, Y. Org. Process Res. Dev. 2019, 23, 2142.
[6] Iwao, O.; Koji, K.; Masami, O. J. Am. Chem. Soc. 1987, 109, 7714.
[7] (a) Ojima, I.; Yatabe, M.; Fuchikami, T. J. Org. Chem. 1982, 47, 2051.
(b) Yarmolchuk, V. S.; Shishkin, O. V.; Starova, V. S.; Zaporozhets, O. A.; Kravchuk, O.; Zozulya, S.; Komarov, I. V.; Mykhailiuk, P. K. Eur. J. Org. Chem. 2013, 2013, 3086.
[8] (a) Feiring, A. E. J. Org. Chem. 1980, 45, 1962.
(b) Mir, Q. C.; Debuhr, R.; Haug, C.; White, H. F.; Gard, G. L. J. Fluorine Chem. 1980, 16, 373.
(c) Zhao, B.; Lu, J.-Y.; Li, Y.; Tu, D.-H.; Liu, Z.-T.; Liu, Z.-W.; Lu, J. RSC Adv. 2015, 5, 101412.
[9] (a) Ma, W.; Lopez, G.; Ameduri, B.; Takahara, A. Langmuir 2020, 36, 1754.
(b) Kostov, G. K.; Lopez, G.; Brandstadter, S. M.; Edwards, B. E.; Améduri, B. Org. Lett. 2014, 16, 3516.
(c) Bruno, A. Macromolecules 2010, 43, 10163.
(d) Kostov, G. K.; Améduri, B.; Brandstadter, S. Collect. Czech. Chem. Commun. 2008, 73, 1747.
[10] (a) Fuchikami, T.; Yatabe, M.; Ojima, I. Synthesis 1981, 365.
(b) Yang, J.; Zhao, H.-W.; He, J.; Zhang, C.-P. Catalysts 2018, 8, 23.
[11] (a) Kraft, B. M.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 2000, 122, 8559.
(b) Kraft, B. M.; Jones, W. D. J. Am. Chem. Soc. 2002, 124, 8681.
(c) Kühnel, M. F.; Lentz, D. Angew. Chem., Int. Ed. 2010, 49, 2933.
(d) Ichitsuka, T.; Fujita, T.; Ichikawa, J. ACS Catal. 2015, 5, 5947.
[12] (a) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1978, 100, 3435.
(b) Lu, X. Rev. Heteroat. Chem. 1991, 4, 278.
(c) Tsuji, J. J. Organomet. Chem. 1986, 300, 281.
[13] Cornella, J.; Edwards, J. T.; Qin, T.; Kawamura, S.; Wang, J.; Pan, C. M.; Gianatassio, R.; Schmidt, M.; Eastgate, M. D.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 2174.
[14] Knochel, P.; Krasovskiy, A. Synthesis 2006, 0890.
[15] Manolikakes, G.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 205.
[16] Ichitsuka, T.; Takanohashi, T.; Fujita, T.; Ichikawa, J. J. Fluorine Chem. 2015, 170, 29.

镍催化下3,3,3-三氟丙烯与芳基锌试剂的区域选择性偶联反应

Nickel-Catalyzed Regioselective Coupling Reaction of 3,3,3-Trifluoropropene with Arylzinc Reagents

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yixin Jiang, Boxiao Tang, Haibo Mao, Xuexia Chen, Yangjie Yu, Cuiying Quan, Zhaoyang Xu, Jinhui Shi, Yilin Liu. A Green, Recyclable and Carrier-Free Study for the Coupling Reaction of Alkenes with Aryl Iodides in H₂O-Polyethylene Glycol (PEG-200) [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3210-3215.
[2]	Yuxing Tong, Ziwei Wang, Ben Liu, Yaowei Xu, Song Gao, Xiangbing Tang, Xinghua Zhang. Recent Advances in Synthesis of 3-Sulfenylated Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1310-1324.
[3]	Yanyan Zhang, Zhuzhu Zhang, Shengqing Zhu, Lingling Chu. Recent Advances in Nickel Catalyzed Asymmetric Acylation Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1023-1035.
[4]	Menghan Shen, Laiqiang Li, Quan Zhou, Jiehui Wang, Lei Wang. Visible-Light-Induced Regio-selective Oxidative Coupling of Quinoxalinones with Pyrrole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 697-704.
[5]	Biao Ma, Miaomiao Zhang, Zhanyu Li, Jinsong Peng, Chunxia Chen. Recent Advance of Transition Metal-Free Catalyzed Suzuki-Type Cross Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 455-470.
[6]	Licheng Wu, Xianqing Wu, Jingping Qu, Yifeng Chen. Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4239-4250.
[7]	Yunpeng Qi, Dengkai Lin, Liang-An Chen. Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3861-3875.
[8]	Weilu Zhang, Shaowei Chen, Xiao Shen. Nickel-Catalyzed [4＋2] Cyclization of Benzosilacyclobutenes and Acylsilanes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3635-3643.
[9]	Wei-Yuan Ma, Huifang Dai, Shaolin Kang, Tianlin Zhang, Xing-Zhong Shu. Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3614-3622.
[10]	Qi Sun, Zeying Sun, Ze Yu, Guangwei Wang. Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2515-2520.
[11]	Xiaojie Liu, Biping Xu, Weiping Su. Rhodium-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling via in-Situ Generation of Acyl Fluorides from Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2184-2191.
[12]	Weiguo Yu, Lingna Wang, Xiaocong Yu, Shuping Luo. Fluorescent Dye/Nickel Synergistic Catalytic Decarboxylative Carbonylation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1216-1223.
[13]	Yurong Zhang, Han Wang, Yongjun Mao, Shiliang Shi. Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1198-1209.
[14]	Zhihao Zhang, Xin Jiang, Qinghan Li. Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 945-964.
[15]	Fufang Wu, Xuejian Li, Hao Jia, Xuanzhen Han, Xiaobao Shen. Iodine(III)-Promoted Oxidative Cross-Coupling Reactions of C—H Bonds via a Free Radical Process [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 884-890.