A Convenient Synthesis of β, β-Difluoro-β-iodo-1-phenylethan-1-ols
- Corresponding author: Wu Fanhong, wfh@sit.edu.cn Wu Jingjing, wjj_693@163.com
Citation:
Huang Guozhi, Ren Jie, Zheng Xiaoxiao, Wu Fanhong, Wu Jingjing. A Convenient Synthesis of β, β-Difluoro-β-iodo-1-phenylethan-1-ols[J]. Chinese Journal of Organic Chemistry,
;2019, 39(12): 3475-3482.
doi:
10.6023/cjoc201905051
Nabi, N.; Agarwal, R.; Mukhopadhyay, H.; Banoo, H.; Nigam, N.; Nigam, N. J. Evol. Med. Dent. Sci. 2017, 6, 215.
doi: 10.14260/Jemds/2017/50
Zheng, L; Zhao, T.; Zou, X. Chin. J. New. Durgs 2015, 24, 361(in Chinese).
Dayer, P.; Desmenles, J.; Collart, L. Drugs 1997, 53, 18.
doi: 10.2165/00003495-199700532-00006
(a) Hiyama, T. Textbook of Organofluorine Compounds: Chemistry and Applications, Springer, New York, 2000.
(b) Gouverneur, V.; Muller, K. Textbook of Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications, Imperial College Press, London, 2012.
(c) Huchet, B.; Kuhn, B.; Wagner, N.; Zimmerli, E. M.; Carreira, K. J. Med. Chem. 2015, 58, 9041.
(d) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
(a) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
(b) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(c) Fu, X. P.; Xiao, Y. L.; Zhang, X. Chin. J. Chem. 2018, 36, 143.
(d) Qi, Q. X.; Zi, Y. Z.; Ling, C. L.; Chuan, F. N.; Jin, B. H. Angew. Chem. Int. Ed. 2019, 58, 6405.
Jagodzinska, M.; Huguenot, F.; Zanda, M. Tetrahedron 2007, 63, 2042.
doi: 10.1016/j.tet.2006.12.045
Yan, C. Z.; Bing, G.; Jin, B. H. J. Am. Chem. Soc. 2012, 134, 5790.
doi: 10.1021/ja301601b
Kosobokov, M. D.; Levin, W.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2014, 16, 3784.
doi: 10.1021/ol501674n
Aikawa, K.; Yoshida, S.; Kondo, D.; Asai, Y.; Mikami, K. Org. Lett. 2015, 17, 5108.
doi: 10.1021/acs.orglett.5b02617
(a) Wang, J. X.; Wu, J. J.; Chen, H.; Zhang, S. W.; Wu, F. H. Chin. Chem Lett. 2015, 26, 1381.
(b) Wang, D. F.; Wu, J. J.; Huang, J. W.; Liang, J. Q.; Peng, P.; Chen, H.; Wu, F. H. Tetrahedron 2017, 73, 3478.
(c) Chen, H.; Wang, J. X.; Wu, J. J.; Kuang, Y. J.; Wu, F. H. J. Fluorine Chem. 2017, 200, 41.
(d) Peng, P.; Wu, J. J.; Wu, F. H. RSC Adv. 2017, 7, 56034.
(e) Liang, J. Q.; Wu, J. J.; Wu, F. H. Adv. Synth. Catal. 2018, 360(11), 2221.
Miyachi, N.; Yanagawa, Y.; Iwasaki, H. Tetrahedron Lett. 1993, 34, 8267.
doi: 10.1016/S0040-4039(00)61407-7
Yang, F. C.; Yang, W. C.; Yang, C.; Wang, H. R.; Sun, K.; Luo, Y. J. Label Compd. Radiopharm. 2016, 59, 313.
doi: 10.1002/jlcr.3400
Toda, F.; Tanaka, K.; Tange, H. J. Chem. Soc., Perkin Trans. 11989, 1555.
Bajwa, N.; Jennings, M. P. J. Org. Chem. 2008, 73, 3638.
doi: 10.1021/jo800150x
Renata, H.; Zhou, Q. H.; Dünstl, G.; Felding, J.; Merchant, R. R.; Baran, P. S. J. Am. Chem. Soc. 2015, 137, 1330.
doi: 10.1021/ja512022r
Miao, W. J.; Ni, C. F.; Zhao, Y. C.; Jin, B. H. Org Lett. 2016, 18, 2766.
doi: 10.1021/acs.orglett.6b01258
Deng, Z. Y.; Lin, J. H.; Ji, C.; Xiao, J. C. Org Lett. 2016, 18. 3206.
doi: 10.1021/acs.orglett.6b01425
Takamasa, F.; Toshinori, H. JP 05230075, 1993.
Panferova, L. I.; Struchkova, M. I.; Dilman, A. D. Synthesis 2017, 49(18), 4124.
doi: 10.1055/s-0036-1590855
Wen, X. L.; Qing, J. L.; Ji, L. L.; Hong, G. W. Angew. Chem. Int. Ed. 2018, 57(50), 16544.
doi: 10.1002/anie.201810204
Dilman, A.; Panferova, L.; Struchkova, M. Synthesis 2017, 49(18), 4124.
doi: 10.1055/s-0036-1590855
Panferova, L. I.; Struchkova, M. I.; Dilman, A. D. Eur. J. Org. Chem. 2018, 27, 3834.
Zhao, Y.; Huang, W.; Zheng, J.; Jin, B. H. Org Lett. 2011, 13(19), 5342.
doi: 10.1021/ol202208b
Capriel, P.; Binsch, G. Tetrahedron 1979, 35(22), 2661.
doi: 10.1016/0040-4020(79)87047-7
Peng, P.; Wu, J.; Liang, J.; Zhang, T.; Huang, J.; Wu, F. RSC Advances. 2017, 7(88), 56034.
doi: 10.1039/C7RA12130J
Bergmann, F.; Kalmus, A.; Breuer, E. J. Am. Chem. Soc. 1958, 80, 4540.
doi: 10.1021/ja01550a029
Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
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
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce4ⅢCe6Ⅳ(μ3-O)4(μ4-O)4(acac)14(CH3O)6]·2CH3OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
Yang Chen , Peng Chen , Yuyang Song , Yuxue Jin , Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077
Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
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
Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
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
Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
.
CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
. CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb2+ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V2O5/TiO2 catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210