Visible Light Promoted Carbodifluoroalkylation of Homopropargylic Alcohols via Concomitant 1, 4-Aryl Migration
- Corresponding author: Zhu Chengjian, cjzhu@nju.edu.cn
Citation: Zhou Nengneng, Xu Pan, Li Weipeng, Cheng Yixiang, Zhu Chengjian. Visible Light Promoted Carbodifluoroalkylation of Homopropargylic Alcohols via Concomitant 1, 4-Aryl Migration[J]. Acta Chimica Sinica, ;2017, 75(1): 60-65. doi: 10.6023/A16070375
(a) Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993. (b) Romanenko, V. D.; Kukhar, V. P. Chem. Rev. 2006, 106, 3868. (c) Muller, K.; Faeh, C.; Diederich, F.; Science 2007, 317, 1881. (d) Furuya, T.; Kuttruff, C.; Ritter, T.; Curr. Opin.Drug Discovery Dev. 2008, 11, 80. (e) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, 2009. (f) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed.2013, 52, 8214. (g) Ni, C.; Zhu, L.; Hu, J. Acta Chim. Sinica 2015, 73, 90. (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.). (h) Zhang, K.; Xu, X.; Qing, F. Chin. J. Org. Chem. 2015, 35, 556. (张柯, 徐修华, 卿凤翎, 有机化学, 2015, 35, 556.)
For some reviews on fluorination, see: (a) Grushin, V. V. Acc. Chem. Res. 2010, 43, 160. (b) Cahard, D.; Xu, X.; Couve-Bonnaire, S.; Pannecoucke, X. Chem. Soc. Rev. 2010, 39, 558. (c) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470. (d) Lin, A.; Huehls, B.; Yang. J. Org. Chem. Front. 2014, 1, 434. For recent examples, see: (e) Li, W.; Zhu, Y.; Duan, Y.; Zhang, M.; Zhu, C. Adv. Synth. Catal. 2015, 357, 1277. (f) Shen, X.; Miao, W.; Ni, C.; Hu, J. Angew. Chem., Int. Ed. 2014, 53, 775. (g) Shen, X.; Min, Z.; Ni, C.; Zhang, W.; Hu, J. Chem. Sci. 2014, 5, 117.
For some reviews on trifluoromethylation, see: (a) Nie, J.; Guo, H.; Cahard, D.; Ma, J. Chem. Rev. 2011, 111, 455. (b) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475. (c) Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950. (d) Furuya, T.; , Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470. For recent examples, see: (e) Gao, P.; Shen, Y. W.; Fang, R.; Hao, X. H.; Qiu, Z. H.; Yang, F.; Yan, X. B.; Gong, X. J.; Liu, X. Y.; Liang, Y. M. Angew. Chem., Int. Ed. 2014, 53, 7629. (f) Liu, J. B.; Chen, C.; Chu, L. L.; Qing. F. L. Angew. Chem., Int. Ed. 2015, 54, 11839. (g) Sahoo, B.; Li, J. L.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 11577.
For recent examples, see: (a) Li, L.; Wang, F.; Ni, C.; Hu, J. Angew. Chem., Int. Ed. 2013, 52, 12390. (b) Min, Q.; Yin, Z.; Feng, Z.; Guo, W.; Zhang, X. J. Am. Chem. Soc. 2014, 136, 1230. (c) Feng, Z.; Min, Q.; Xiao, Y.; Zhang, B.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 1669. (d) Wang, X.; Liu, G.; Xu, X.; Shibata, N.; Tokunaga, E.; Shibata, N. Angew. Chem., Int. Ed. 2014, 53, 1827. (e) Chang, D.; Gu, Y.; Shen, Q. Chem. Eur. J. 2015, 21, 6074. (f) He, Y. T.; Wang, Q.; Li, L. H.; Liu, X. Y.; Xu, P. F.; Liang, Y. M. Org. Lett. 2015, 17, 5188. (g) Lin, Q. Y.; Xu, X. H.; Zhang, K.; Qing, F. L. Angew. Chem., Int. Ed. 2016, 55, 1479. (h) Xie, J.; Zhang, T.; Chen, F. Mehrkens, N.; Rominger, F.; Rudolph, M.; Hashmi, A. S. Angew. Chem., Int. Ed. 2016, 55, 2934.
(a) Blackburn, C. M.; England, D. A.; Kolkmann, F. J. Chem. Soc. Chem. Commun. 1981, 930. (b) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Perkin Trans. 1 1984, 1119. (c) Erickson, J. A.; Mcloughlin, J. I. J. Org. Chem. 1995, 60, 1626. (d) Kitazume, T.; Kamazaki, T. Experimental Methods in Organic Fluorine Chemistry, Gordon and Breach Science, Tokyo, 1998.
For recent reviews on photoredox catalysis, see: (a) Xuan, J.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 6828. (b) Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527. (c) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102. (d) Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617. (e) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322; (f) Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387. (g) Xie, J.; Jin, H.; Xu, P.; Zhu, C. Tetrahedron Lett. 2014, 55, 36.
(a) Yu, C.; Iqbal, N.; Park, S.; Cho, E. Chem. Commun. 2014, 50, 12884. (b) Sun, X.; Yu, S. Org. Lett. 2014, 16, 2398. (c) Su, Y. M.; Hou, Y.; Yin, F.; Xu, Y. M.; Li, Y.; Zheng, X.; Wang, X. S.; Org. Lett. 2014, 16, 2958. (d) Wang, L.; Wei, X.; Jia, W.; Zhong, J.; Wu. L.; Liu, Q. Org. Lett. 2014, 16, 5842. (e) Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160. (f) Wallentin, C. J.; Nguyen, J. D.; Finkbeiner. P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875. (g) Jung, J.; Kim, E.; You. Y.; Cho, E. Adv. Synth. Catal. 2014, 356, 2741. (h) Gu, Z. X.; Zhang, H. L.; Xu, P.; Cheng, Y. X.; Zhu. C. J. Adv. Synth. Catal. 2015, 357, 3057. (j) Xu, P.; Hu, K. D.; Gu, Z. X.; Cheng, Y. X.; Zhu, C. J. Chem. Commun. 2015, 51, 7222.
(a) Li, W.; Zhu, X.; Mao, H.; Tang, Z.; Cheng, Y.; Zhu, C. Chem. Commun. 2014, 50, 7521. (b) Qu, C. H.; Xu, P.; Ma, W. J.; Cheng, Y. X.; Zhu, C. J. Chem. Commun. 2015, 51, 13508. (c) Gu, Z. X.; Zhang, H. L.; Xu, P.; Cheng, Y. X.; Zhu, C. J. Adv. Synth. Catal. 2015, 357, 3057. (d) Xu, P.; Wang, G. Q.; Zhu, Y. C.; Li, W. P.; Cheng, Y. X.; Li, S. H.; Zhu, C. J. Angew. Chem., Int. Ed. 2016, 55, 2939.
For reviews on aryl migration: (a) Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649. (b) Chen, Z. M.; Zhang, X. M.; Tu, Y. Q. Chem. Soc. Rev. 2015, 44, 5220.
For the aryldifluoroacetylation of alkynes reaction, see: Fu, W. J.; Zhu, M.; Zou, G. L.; Xu, C.; Wang, Z. Q.; Ji, B. M. J. Org. Chem. 2015, 80, 4766.
Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C3N4 nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
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
Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO2 reduction performance of Z-scheme Ag-Cu2O/BiVO4 photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434
Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H2O2 Production and Cr(VI) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag3PO4/C3N5 Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-. doi: 10.3866/PKU.WHXB202310013
Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn2+ doped quasi-two-dimensional perovskites (PEA)2PbyMn1-yBr4. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
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
Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO2 reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H2 production activity of BaTiO3 nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
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
Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO2 methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
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
Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO2 cycloaddition over W18O49/NH2-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
Qiang ZHAO , Zhinan GUO , Shuying LI , Junli WANG , Zuopeng LI , Zhifang JIA , Kewei WANG , Yong GUO . Cu2O/Bi2MoO6 Z-type heterojunction: Construction and photocatalytic degradation properties. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 885-894. doi: 10.11862/CJIC.20230435
Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346