Oxidative Coupling Reactions of Arylboronic Acids and Fluoroform-Derived AgCF3

doi:10.6023/cjoc202005022

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3426-3430.DOI: 10.6023/cjoc202005022 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

芳基硼酸和氟仿衍生三氟甲基银的氧化偶联反应

欧阳瑶, 徐修华, 卿凤翎

中国科学院上海有机化学研究所分子合成卓越中心有机氟化学重点实验室上海 200032

收稿日期:2020-05-09 修回日期:2020-06-03 发布日期:2020-06-10
通讯作者: 卿凤翎 E-mail:flq@mail.sioc.ac.cn
基金资助:
国家自然科学基金（Nos.21421002，21991211）和中国科学院战略先导研究计划（No.XDB20000000）资助项目.

Oxidative Coupling Reactions of Arylboronic Acids and Fluoroform-Derived AgCF₃

Ouyang Yao, Xu Xiuhua, Qing Fengling

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

Received:2020-05-09 Revised:2020-06-03 Published:2020-06-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21421002, 21991211) and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000).

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Ouyang Yao, Xu Xiuhua, Qing Fengling. Oxidative Coupling Reactions of Arylboronic Acids and Fluoroform-Derived AgCF₃[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3426-3430.

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[1] (a) Purser, S.; Moor, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(b) Cametti, M.; Crousse, B.; Metrangolo, P.; Milani, R.; Resnati, G. Chem. Soc. Rev. 2012, 41, 31.
(c) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; delPozo, C. A.; Sorochinsky, E.; Fustero, S. V.; Soloshonok, A.; Liu, H. Chem. Rev. 2014, 114, 2432.
(d) Meanwell, N. A. J. Med. Chem. 2018, 61, 5822.
[2] (a) Mullard, A. Nat. Rev. Drug Discovery 2018, 17, 81.
(b) Mullard, A. Nat. Rev. Drug Discovery 2019, 18, 85.
(c) Mullard, A. Nat. Rev. Drug Discovery 2020, 19, 79.
[3] For selected reviews, see:(a) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.
(b) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.
(c) Besset, T.; Schneider, C.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 5048.
(d) Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815(in Chinese). (卿凤翎, 有机化学, 2012, 32, 815.)
(e) Macé, Y.; Magnier, E. Eur. J. Org. Chem. 2012, 2479.
(f) Landelle, G.; Panossian, A.; Pazenok, S.; Vors, J.-P.; Leroux, F. R. Beilstein J. Org. Chem. 2013, 9, 2476.
(g) Chen, P.; Liu, G. Synthesis 2013, 45, 2919.
(h) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513.
(i) Wang, G.; He, X.; Dai, J.; Xu, H. Chin. J. Org. Chem. 2014, 34, 837(in Chinese). (王光祖, 赫侠平, 戴建军, 许华建, 有机化学, 2014, 34, 837.)
(j) Charpentier, J.; Früh, N.; Togni, A. Chem. Rev. 2015, 115, 650.
(k) Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683.
(l) Alonso, C.; de Marigorta, E. M.; Rubiales, G.; Palacios, F. Chem. Rev. 2015, 115, 1847.
(m) Liu, Q.; Ni, C.; Hu, J. Natl. Sci. Rev. 2017, 4, 303.
(n) Ji, X.; Shi, G.; Zhang, Y. Chin. J. Org. Chem. 2019, 39, 929(in Chinese). (季小明, 史广法, 张扬会, 有机化学, 2019, 39, 929.)
[4] For selected examples, see:(a) Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909.
(b) Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679.
(c) Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Angew. Chem., Int. Ed. 2011, 50, 1896.
(d) Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K.-W. Organometallics 2011, 30, 3229.
(e) Li, X.; Zhao, J.; Zhang, L.; Hu, M.; Wang, L.; Hu, J. Org. Lett. 2015, 17, 298.
(f) Wei, Y.; Yu, L.; Lin, J.; Zheng, X.; Xiao, J. Chin. J. Chem. 2016, 34, 481.
(g) Le, C.; Chen, T. Q.; Liang, T.; Zhang, P.; MacMillan, D. W. C. Science 2018, 360, 1010.
[5] (a) Danoun, G.; Bayarmagnai, B.; Grunberg, M. F.; Gooßen, L. J. Angew. Chem., Int. Ed. 2013, 52, 7972.
(b) Wang, X.; Xu, Y.; Mo, F.; Ji, G.; Qiu, D.; Feng, J.; Ye, Y.; Zhang, S.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2013, 135, 10330.
(c) Dai, J.-J.; Fang, C.; Xiao, B.; Yi, J.; Xu, J.; Liu, Z.-J.; Lu, X.; Liu, L. Fu, Y. J. Am. Chem. Soc. 2013, 135, 8436.
(d) Lishchynskyi, A.; Berthon, G.; Grushin, V. V. Chem. Commun. 2014, 50, 10237.
(e) Zhang, K.; Xu, X.-H.; Qing, F.-L. J. Org. Chem. 2015, 80, 7658.
(f) Hong, J.; Wang, G.; Huo, L.; Zheng, C. Chin. J. Chem. 2017, 35, 1761.
[6] Ye, F.; Berger, F.; Jia, H.; Ford, J.; Wortman, A.; Börgel, J.; Genicot, C.; Ritter, T. Angew. Chem., Int. Ed. 2019, 58, 14615.
[7] (a) Yang, J.-Y.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2015, 180, 175.
(b) Yang, J.-Y.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2016, 186, 45.
(c) Pandey, V. K.; Anbarasan, P. RSC Adv. 2016, 6, 18525.
[8] (a) Wang, X.-S.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648.
(b) Mu, X.; Chen, S.; Zhen, X.; Liu, G. Chem.-Eur. J. 2011, 17, 6039.
(c) Pan, F.; Shi, Z. Acta Chim. Sinica 2012, 70, 1679(in Chinese). (潘菲, 施章杰, 化学学报, 2012, 70, 1679.)
(d) Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298.
(e) Zhang, X.-G.; Dai, H.-X.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 11948.
(f) Shang, M.; Sun, S.-Z.; Wang, H.-L.; Laforteza, B. N.; Dai, H.-X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2014, 53, 10439.
[9] (a) Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060.
(b) Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174.
(c) Jiang, X.; Chu, L.; Qing, F.-L. J. Org. Chem. 2012, 77, 1251.
(d) Nguyen, T. V.; Ong, T. D.; Lam, A. H. M.; Pham, V. T.; Phan, N. T. S.; Truong, T. Mol. Catal. 2017, 436, 60.
[10] (a) Xu, J.; Luo, D.-F.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300.
(b) Zhang, C.-P.; Cai, J.; Zhou, C.-B.; Wang, X.-P.; Zheng, X.; Gu, Y.-C.; Xiao, J.-C. Chem. Commun. 2011, 47, 9516.
(c) Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342.
[11] (a) Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034.
(b) Ye, Y.; Künzi, S. A.; Sanford, M. S. Org. Lett. 2012, 14, 4979.
(c) Li, Y.; Wu, L.; Neumann, H.; Beller, M. Chem. Commun. 2013, 49, 2628.
[12] (a) Novák, P.; Lishchynskyi, A.; Grushin, V. V. Angew. Chem., Int. Ed. 2012, 51, 7767.
(b) van der Born, D.; Sewing, C.; Herscheid, J. D. M.; Windhorst, A. D.; Orru, R. V. A.; Vugts, D. J. Angew. Chem., Int. Ed. 2014, 53, 11046.
(c) Ivashkin, P.; Lemonnier, G.; Cousin, J.; Grégoire, V.; Labar, D.; Jubault, P.; Pannecoucke, X. Chem.-Eur. J. 2014, 20, 9514.
[13] (a) Zhang, S.-L.; Bie, W.-F. Dalton Trans. 2016, 45, 17588.
(b) Zhang, S.-L.; Bie, W.-F. RSC Adv. 2016, 6, 70902.
(c) Zhang, S.-L.; Xiao, C.; Wan, H.-X. Dalton Trans. 2018, 47, 4779.
(d) Xiao, C.; Zhang, S.-L. Dalton Trans. 2019, 48, 848.
[14] Xiang, J.-X.; Ouyang, Y.; Xu, X.-H.; Qing, F.-L. Angew. Chem., Int. Ed. 2019, 58, 10320.
[15] (a) Liu, J.-B.; Chen, C.; Chu, L.; Chen, Z.-H.; Xu, X.-H.; Qing, F.-L. Angew. Chem., Int. Ed. 2015, 54, 11839.
(b) Liu, J.-B.; Xu, X.-H.; Qing, F.-L. Org. Lett. 2015, 17, 5048.
(c) Fu, M.-L.; Liu, J.-B.; Xu, X.-H.; Qing, F.-L. J. Org. Chem. 2017, 82, 3702.
(d) Zhang, K.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2017, 196, 24.
(e) Xiang, J.-X.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2017, 203, 110.
(f) Zhu, S.-Q.; Liu, Y.-L.; Li, H.; Xu, X.-H.; Qing, F.-L. J. Am. Chem. Soc. 2018, 140, 11613.
[16] (a) Tyrra, W.; Naumann, D. J. Fluorine Chem. 2004, 125, 823.
(b) Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem. Soc. 2013, 135, 2955.
[17] (a) Ye, Y.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464.
(b) Hafner, A.; Bräse, S. Angew. Chem., Int. Ed. 2012, 51, 3713.
(c) Wu, X.; Chu, L.; Qing, F.-L. Angew. Chem., Int. Ed. 2013, 52, 2198.
(d) Mao, Z.; Huang, F.; Yu, H.; Chen, J.; Yu, Z.; Xu, Z. Chem.-Eur. J. 2014, 20, 3439.
(e) Lin, J.-S.; Liu, X.-G.; Zhu, X.-L.; Tan, B.; Liu, X.-Y. J. Org. Chem. 2014, 79, 7084.
(f) Teng, F.; Cheng, J.; Bolm, C. Org. Lett. 2015, 17, 3166.
(g) Wu, Y.-B.; Lu, G.-P.; Yuan, T.; Xu, Z.-B.; Wan, L.; Cai, C. Chem. Commun. 2016, 52, 13668.
(h) Harris, C. F.; Kuehner, C. S.; Bacsa, J.; Soper, J. D. Angew. Chem., Int. Ed. 2018, 57, 1311.
[18] (a) Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K.-W. Organometallics 2011, 30, 3229.
(b) de Salinas, S. M.; Mudarra, Á. L.; Benet-Buchholz, J.; Parella, T.; Maseras, F.; Pérez-Temprano, M. H. Chem.-Eur. J. 2018, 24, 11895.
[19] (a) Fukuyama, T.; Nishikawa, T.; Ruy, I. Eur. J. Org. Chem. 2020, 1424.
(b) Deng, Y.; Lu, F.; You, S.; Xia, T.; Zheng, Y.; Lu, C.; Yang, G.; Chen, Z.; Gao, M.; Lei, A. Chin. J. Chem. 2019, 37, 817.
(c) Wang, H.; Wang, J.; Qiu, W.; Yang, F.; Liu, X.; Tang, J. Chin. J. Chem. 2010, 28, 2416.
(d) Lin, L.; Hou, C.; Li, H.; Weng, Z. Chem.-Eur. J. 2016, 22, 2075.
(e) Cottet, F.; Schlosser, M. Eur. J. Org. Chem. 2002, 327.

芳基硼酸和氟仿衍生三氟甲基银的氧化偶联反应

Oxidative Coupling Reactions of Arylboronic Acids and Fluoroform-Derived AgCF₃

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[1]	Yan Xiaohui, Li Jiarong, Zhang Qi, Shi Daxin. Synthesis of Nitroarenes under Microwave [J]. Chin. J. Org. Chem., 2017, 37(6): 1450-1455.
[2]	Xu Qing, Jia Xiaojuan, Li Xiaohui, Sun Qing, Zhou Yongbo, Yin Shuangfeng, Han Libiao. Copper-Catalyzed Aerobic Oxidative C-P Coupling of Arylboronic Acids and Diethyl Phosphite under Air [J]. Chin. J. Org. Chem., 2014, 34(7): 1340-1346.
[3]	YOU TIANPA;H.S.HOSHER.K.OKAMOTO. A new chiral reagent for measuring the enantiomeric purity of chiral acids [J]. Chin. J. Org. Chem., 1990, 10(6): 498-503.
[4]	YOU TIANPA;H.S.Mosher. Synthesis and study of a new chiral agent-R-(-)-β-trifluoromethyl-β -methoxy-β-phenylethylamine [J]. Chin. J. Org. Chem., 1989, 9(6): 518-520.