Fluorodecarboxylation of β, γ-Unsaturated Carboxylic Acids Using Trivalent Iodine and Hydrofluoric Acid-Based Fluorination Reagent
- Corresponding author: Yi Wenbin, yiwb@njust.edu.cn
Citation: Song Zhidong, Jiang Lvqi, Yi Wenbin. Fluorodecarboxylation of β, γ-Unsaturated Carboxylic Acids Using Trivalent Iodine and Hydrofluoric Acid-Based Fluorination Reagent[J]. Acta Chimica Sinica, ;2018, 76(12): 967-971. doi: 10.6023/A18080321
(a) Singh, O. V.; Han, H. Org. Lett. 2007, 9, 4801; (b) Mizuno, S.; Terasaki, S.; Shinozawa, T.; Kawatsura, M. Org. Lett. 2017, 19, 504. (c) Wu, R. H.; Yang, W.; Cheng, G.; Li, Y.; Yang, D. Q. Chinese J. Org. Chem. 2016, 36, 2368(in Chinese). (仵瑞华, 杨文, 程果, 李玥, 杨定乔, 有机化学, 2016, 36, 2368); (d) Chen, C. H.; Fu, L.; Chen, P. H.; Liu, G. S. Chin. J. Chem. 2017, 35, 1781; (e) Gu, Y.; Lu, C.; Gu, Y.; Shen, Q. Chin. J. Chem. 2018, 36, 55.
(a) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Wiley-VCH, Weinheim, Germany, 2004; (b) Hiyama, T. Organofluorine Compounds: Chemistry and Applications, Springer, Berlin, 2000; (c) Uneyama, K. Organofluorine Chemistry, Blackwell, Oxford, U.K., 2006; (d) Richard, C. Fluorine in Organic Chemistry, CRC Press, Boca Raton, FL, 2004.
(a) Honda, T.; Liby, K. T.; Su, X.; Sundararajan, C.; Honda, Y.; Suh, N.; Risingsong, R.; Williams, C. R.; Royce, D. B.; Sporn, M. B.; Gribble, G. W. Bioorg. Med. Chem. Lett. 2006, 16, 6306; (b) Kaneko, S.; Arai, M.; Uchida, T.; Harasaki, T.; Fukuoka, T.; Konosu, T. Bioorg. Med. Chem. Lett. 2002, 12, 1705; (c) Rothman, S. C.; Johnston, J. B.; Lee, S.; Walker, J. R.; Poulter, C. D. J. Am. Chem. Soc. 2008, 130, 4906; (d) Leblanc, Y.; Roy, P.; Leger, S.; Grimm, E.; Wang, Z. WO 9841516, 1998[Chem. Abstr. 1998, 129, 275831].
(a) Walkowiak-Kulikowska, J.; Szwajca, A.; Boschet, F.; Gouverneur, V.; Ameduri, B. Macromolecules 2014, 47, 8634. (b) Kostov, G.; Tredwell, M.; Gouverneur, V.; Ameduri, B. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 3843. (c) Wall, L. A. Fluoropolymers, Wiley, New York, 1972.
Hollingworth, C.; Hazari, A.; Hopkinson, M. N.; Tredwell, M.; Benedetto, E.; Huiban, M.; Gee, A. D.; Brown, J. M.; Gouverneur, V. Angew. Chem., Int. Ed. 2011, 50, 2613.
doi: 10.1002/anie.201007307
Walkowiak, J.; Martinez, D. C. T.; Ameduri, B.; Gouverneur, V. Synthesis 2010, 1883.
(a) Kirihara, M.; Kambayashi, T.; Momose, T. Chem. Commun. 1996, 1103; (b) Kirihara, M.; Kakuda, H.; Tsunooka, M.; Shimajiri, A.; Takuwa, T.; Hatano, A. Tetrahedron Lett. 2003, 44, 8513.
Hu, J. B.; He, Z. B. CN 102219638, 2011[Chem. Abstr. 2011, 155, 588760].
(a) He, Z. B.; Ping, T.; Hu, J. B. Org. Lett. 2016, 18, 72; (b) Ma, J. J.; Yi, W. B.; Lu, G. P.; Cai, C. Adv. Synth. Catal. 2015, 357, 3447. (c) Xu, X. L.; Chen, H. H.; He, J. B.; Xu, H. J. Chin. J. Chem. 2017, 35, 1665; (d) Montazerozohori, M.; Nasr-Esfahani, M.; Akhlaghi, P. Chin. J. Chem. 2009, 27, 1007; (e) Zhang, J. J.; Cheng, Y. B.; Duan, X. H. Chin. J. Chem. 2017, 35, 311; (f) Zhao, Y. W.; Feng, Q.; Song, Q. L. Chin. Chem. Lett. 2016, 27, 571.
(a) Chatalova-Sazepin, C.; Binayeva, M.; Epifanov, M.; Zhang, W.; Foth, P.; Amador, C.; Jagdeo, M.; Boswell, B. R.; Sammis, G. M. Org. Lett. 2016, 18, 4570; (b) Patrick, T. B.; Khazaeli, S.; Nadji, S.; Hering-Smith, K.; Reif, D. J. Org. Chem. 1993, 58, 705.
(a) Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401; (b) Zhang, X. Comput. Theor. Chem. 2016, 1082, 11; (c) Zhang, Q. W.; Brusoe, A. T.; Mascitti, V.; Hesp, K. D.; Blakemore, D. C.; Kohrt, J. T.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 9758; (d) Mizuta, S.; Stenhagen, I. S. R.; O'Duill, M.; Wolstenhulme, J.; Kirjavainen, A. K.; Forsback, S. J.; Tredwell, M.; Sandford, G.; Moore, P. R.; Huiban, M.; Luthra, S. K.; Passchier, J.; Solin, O.; Gouverneur, V. Org. Lett. 2013, 15, 2648.
(a) Leung, J. C. T.; Chatalova-Sazepin, C.; West, J. G.; Rueda-Becerril, M.; Paquin, J. F.; Sammis, G. M. Angew. Chem., Int. Ed. 2012, 51, 10804; (b) Leung, J. C. T.; Sammis, G. M. Eur. J. Org. Chem. 2015, 2197; (c) Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654; (d) Wang, D. H.; Yuan, Z. L.; Liu, Q. L.; Chen, P. H. Liu, G. S. Chin. J. Chem. 2018, 36, 507; (e) Dong, Y.; Wang, Z.; Li, C. Nat. Commun. 2017, 8, 277.
Rueda-Becerril, M.; Chatalova Sazepin, C.; Leung, J. C. T.; Okbinoglu, T.; Kennepohl, P.; Paquin, J. F.; Sammis, G. M. J. Am. Chem. Soc. 2012, 134, 4026.
doi: 10.1021/ja211679v
Yang, Q.; Mao, L. L.; Yang, B.; Yang, S. D. Org. Lett. 2014, 16, 3460.
doi: 10.1021/ol501357w
(a) Fagnou, K.; Lautens, M. Angew. Chem. 2002, 114, 26; (b) Yan, N.; Lei, Z. W.; Su, J. K.; Liao, W. L. Hu, X. G. Chin. Chem. Lett. 2017, 28, 467; (c) Wang, L. Y.; Jiang, X. H.; Tang, P. P. Org. Chem. Front. 2017, 4, 1958.
(a) Katcher, M. H.; Sha, A.; Doyle, A. G. J. Am. Chem. Soc. 2011, 133, 15902; (b) Lee, E.; Hooker, J. M.; Ritter, T. J. Am. Chem. Soc. 2012, 134, 17456; (c) Fier, P. S.; Luo, J.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2552; (d) Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 10795; (e) Liu, Z.; Chen, H.; Lv, Y.; Tan, X.; Shen, H.; Yu, H.-Z.; Li, C. J. Am. Chem. Soc. 2018, 140, 6169; (f) Ma, J. A.; Li, S. Org. Chem. Front. 2014, 1, 712.
Woerly, E. M.; Banik, S. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2016, 138, 13858.
doi: 10.1021/jacs.6b09499
Huang, X.; Liu, W.; Hooker, J. M.; Groves, J. T. Angew. Chem., Int. Ed. 2015, 54, 5241.
doi: 10.1002/anie.v54.17
(a) Souto, J. A.; Becker, P.; Iglesias, A.; Muñiz, K. J. Am. Chem. Soc. 2012, 134, 15505; (b) Souto, J. A.; Martínez, C.; Velilla, I.; Muñiz, K. Angew. Chem., Int. Ed. 2013, 52, 324; (c) Röben, C.; Souto, J. A.; Escudero-Adán, E. C.; Muñiz, K. Org. Lett. 2013, 15, 1008; (d) Farid, U.; Malmedy, F.; Claveau, R.; Albers, L.; Wirth, T. Angew. Chem., Int. Ed. 2013, 52, 7018; (e) Wang, Y.; Wang, Y.; Zhang, Q.; Li, D. Org. Chem. Front. 2017, 4, 514; (f) Gao, P.; Fan, M. J.; Bai, Z. J.; Wei, Y. Y. Chin. J. Chem. 2015, 33, 479.
(a) Kiyokawa, K.; Yahata, S.; Kojima, T.; Minakata, S. Org. Lett. 2014, 16, 4646; (b) Kiyokawa, K.; Kojima, T.; Hishikawa, Y.; Minakata, S. Chem. Eur. J. 2015, 21, 15548.
(a) Jiang, L. Q.; Qian, J. L.; Yi, W. B.; Lu, G. P.; Cai, C.; Zhang, W. Angew. Chem., Int. Ed. 2015, 54, 14965; (b) Lin, Y.-M.; Yi, W. B.; Shen, W. Z.; Lu, G. P. Org. Lett. 2016, 18, 592; (c) Song, Z. D.; Yi, W. B. Adv. Synth. Catal. 2016, 358, 2727.
(a) Kitamura, T.; Muta, K.; Kuriki, S. Tetrahedron Lett. 2013, 54, 6118; (b) Carpenter, W. J. Org. Chem. 1966, 31, 2688; (c) Zupan, M.; Pollak, A. J. Fluorine Chem. 1976, 7, 445; (d) Arrica, M. A.; Wirth, T. Eur. J. Org. Chem. 2005, 395; (e) Ye, C.; Twamley, B.; Shreeve, J. M. Org. Lett. 2005, 7, 3961.
Kitamura, T.; Muta, K.; Oyamada, J. J. Org. Chem. 2015, 80, 10431.
doi: 10.1021/acs.joc.5b01929
Li, Y.; Ni, C.; Liu, J.; Zhang, L.; Zheng, J.; Zhu, L.; Hu, J. B. Org. Lett. 2006, 8, 1693.
doi: 10.1021/ol060322t
(a) Fukuzumi, T.; Shibata, N.; Sugiura, M.; Yasui, H.; Nakamura, S.; Toru, T. Angew. Chem., Int. Ed. 2006, 45, 4973; (b) Furukawa, T.; Shibata, N.; Mizuta, S.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 8051.
Prakash, G. K. S.; Ledneczki, I.; Chacko, S.; Olah, G. A. Org. Lett. 2008, 10, 557.
doi: 10.1021/ol702500u
Traff, A. M.; Janjetovic, M.; Ta, L.; Hilmersson, G. Angew. Chem., Int. Ed. 2013, 52, 12073.
doi: 10.1002/anie.201306104
(a) Yi, W. B.; Huang, X.; Zhang, Z.; Zhu, D.; Cai, C.; Zhang, W. Green Chem. 2012, 14, 3185; (b) Qian, J. L.; Yi, W. B.; Huang, X.; Miao, Y. B.; Zhang, J. K.; Cai, C.; Zhang, W. Org. Lett. 2015, 17, 1090; (c) Song, Z. D.; Huang, X.; Yi, W. B.; Zhang, W. Org. Lett. 2016, 18, 5640.
Benedetto, E.; Keita, M.; Tredwell, M.; Hollingworth, C.; Brown, J. M.; Gouverneur, V. Organometallics 2012, 31, 1408.
Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
Zhihuan XU , Qing KANG , Yuzhen LONG , Qian YUAN , Cidong LIU , Xin LI , Genghuai TANG , Yuqing LIAO . Effect of graphene oxide concentration on the electrochemical properties of reduced graphene oxide/ZnS. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1329-1336. doi: 10.11862/CJIC.20230447
Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO2 with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
Ruiqing LIU , Wenxiu LIU , Kun XIE , Yiran LIU , Hui CHENG , Xiaoyu WANG , Chenxu TIAN , Xiujing LIN , Xiaomiao FENG . Three-dimensional porous titanium nitride as a highly efficient sulfur host. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 867-876. doi: 10.11862/CJIC.20230441
Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO2-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
Zeyu XU , Anlei DANG , Bihua DENG , Xiaoxin ZUO , Yu LU , Ping YANG , Wenzhu YIN . Evaluation of the efficacy of graphene oxide quantum dots as an ovalbumin delivery platform and adjuvant for immune enhancement. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1065-1078. doi: 10.11862/CJIC.20240099
Hao BAI , Weizhi JI , Jinyan CHEN , Hongji LI , Mingji LI . Preparation of Cu2O/Cu-vertical graphene microelectrode and detection of uric acid/electroencephalogram. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1309-1319. doi: 10.11862/CJIC.20240001
Peng XU , Shasha WANG , Nannan CHEN , Ao WANG , Dongmei YU . Preparation of three-layer magnetic composite Fe3O4@polyacrylic acid@ZiF-8 for efficient removal of malachite green in water. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 544-554. doi: 10.11862/CJIC.20230239