PhSO3CH2F: 一种用于乙酰丙酮衍生物O-一氟甲基化的新型试剂
收稿日期: 2022-03-01
修回日期: 2022-06-01
网络出版日期: 2022-07-14
基金资助
国家自然科学基金(21776138); 国家自然科学基金(22078161); 国家自然科学基金(22108124); 中央高校基本科研业务费专项资金(30918011314); 江苏省自然科学基金(BK20141394); 江苏省青蓝工程((2022)29); 江苏省青蓝工程
PhSO3CH2F: A New Reagent for O-Monofluoromethylation of Acetylacetone Derivatives
Received date: 2022-03-01
Revised date: 2022-06-01
Online published: 2022-07-14
Supported by
National Natural Science Foundation of China(21776138); National Natural Science Foundation of China(22078161); National Natural Science Foundation of China(22108124); Fundamental Research Funds for the Central Universities(30918011314); Natural Science Foundation of Jiangsu Province(BK20141394); Six Talent Peaks Project in Jiangsu Province
李珊 , 蒋绿齐 . PhSO3CH2F: 一种用于乙酰丙酮衍生物O-一氟甲基化的新型试剂[J]. 有机化学, 2022 , 42(11) : 3798 -3804 . DOI: 10.6023/cjoc202203004
A new shelf-stable and easily scalable monofluoromethylating reagent, fluoromethyl benzenesulfonate (PhSO3CH2F), was developed. This reagent is able to react with acetylacetone derivatives to afford corresponding O-monofluoromethylated products in high selectivity and good yields under mild conditions. Moreover, the method could be used in late-stage monofluoromethylation. This method provides more options for the synthesis of monofluoromethyl compounds.
| [1] | (a) Filler, R. Biomedical Aspects of Fluorine Chemistry, Kodansha, Tokyo, 1982. |
| [1] | (b) Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. |
| [1] | (c) Meanwell, N. A. J. Med. Chem. 2011, 54, 2529. |
| [1] | (d) Landelle, G.; Panossian, A.; Leroux, F. R. Curr. Top. Med. Chem. 2014, 14, 941. |
| [2] | (a) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Acena, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422. |
| [2] | (b) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315. |
| [2] | (c) Hagmann, W. K. J. Med. Chem. 2008, 51, 435. |
| [2] | (d) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. |
| [2] | (e) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013. |
| [3] | (a) Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827. |
| [3] | (b) Jeschke, P.; Baston, E.; Leroux, F. R. Mini-Rev. Med. Chem. 2007, 7, 1027, and references therein. |
| [3] | (c) Manteau, B.; Pazenok, S.; Vors, J. P.; Leroux, F. R. J. Fluorine Chem. 2010, 131, 140. |
| [3] | (d) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315. |
| [3] | (e) Tlili, A.; Toulgoat, F.; Billard, T. Angew. Chem., Int. Ed. 2016, 55, 11726. |
| [4] | (a) Kollonitsch, J.; Patchett, A. A.; Marburg, S.; Maycock, A. L.; Perkins, L. M.; Doldouras, G. A.; Duggan, D. E..; Aster, S. D. Nature 1978, 274, 906. |
| [4] | (b) Mckeage, K.; Keam, S. J. Drugs 2009, 69, 1799. |
| [4] | (c) Rojas, R. A.; Paluga, I.; Goldfrad, C. H.; Duggan, M. T.; Barnes, N. Asthma 2007, 44, 437. |
| [5] | (a) Olah, G. A.; Pavlath, A. Acta Chim. Acad. Sci. Hung. 1953, 3, 203. |
| [5] | (b) Olah, G. A.; Pavlath, A. Acta Chim. Acad. Sci. Hung. 1953, 3, 425. |
| [6] | Iwata, R.; Pascali, C.; Bogni, A.; Furumoto, S.; Terasaki, K.; Yanai, K. Appl. Radiat. Isot. 2002, 57, 347. |
| [7] | (a) Rheude, U.; Sundermeyer, W. Chem. Ber. 1985, 118, 2208. |
| [7] | (b) Grozinger, K. G.; Kriwacki, R. W.; Leonard, S. F.; Pitner, T. P. J. Org. Chem. 1993, 58, 709. |
| [7] | (c) Gerus, I. I.; Kolomeitsev, A. A.; Kolycheva, M. I.; Kukhar, V. P. J. Fluorine Chem. 2000, 105, 31. |
| [7] | (d) Gao, M.; Miller, M. A.; DeGrado, T. R.; Mock, B. H.; Lopshire, J. C.; Rosenberger, J. G.; Dusa, C.; Das, M. K.; Groh, W. J.; Zipes, D. P.; Hutchins, G. D.; Zheng, Q. Bioorg. Med. Chem. 2007, 15, 1289. |
| [7] | (e) Zhang, W.; Zhu, L. G.; Hu, J. Tetrahedron 2007, 63, 10569. |
| [8] | (a) Lesuisse, D.; Gourvest, J. F.; Hartmann, C.; Tric, B.; Benslimane, O.; Philibert, D.; Vevert, J. P. J. Med. Chem. 1992, 35, 1588. |
| [8] | (b) Kanai, T.; Kai, Y.; Sato, N.; Naito, T.; Kamiya, T.; Nakamura, T.; Ogura, K. Bull. Chem. Soc. Jpn. 1993, 66, 2335. |
| [8] | (c) Hamill, T. G.; McCauley, J. A.; Burns, H. D. J. Labelled Compd. Radiopharm. 2005, 48, 1. |
| [8] | (d) Donohue, S. R.; Halldin, C.; Pike, V. W. Bioorg. Med. Chem. 2006, 14, 3712. |
| [8] | (e) Chin, F. T.; Morse, C. L.; Shetty, H. U.; Pike, V. W. J. Labelled Compd. Radiopharm. 2006, 49, 17. |
| [8] | (f) An, L.; Xiao, Y.; Min, Q.; Zhang, X. Angew. Chem., Int. Ed. 2015, 54, 9079. |
| [9] | (a) Zheng, L.; Berridge, M. S. Appl. Radiat. Isot. 2000, 52, 55. |
| [9] | (b) Zhang, M.; Maeda, J.; Furutsuka, K.; Yoshida, Y.; Ogawa, M.; Suhara, T.; Suzuki, K. Bioorg. Med. Chem. Lett. 2003, 13, 201. |
| [9] | (c) Hamill, T. G.; Burns, H. D. J. Labelled Compd. Radiopharm. 2004, 47, 99. |
| [9] | (d) Zhang, M.; Maeda, J.; Ito, T.; Okauchi, T.; Ogawa, M.; Noguchi, J.; Suhara, T.; Halldin, C.; Suzuki, K. Bioorg. Med. Chem. 2005, 13, 1811. |
| [9] | (e) Zhang, M.; Ogawa, M.; Furutsuka, K.; Yoshida, Y.; Suzuki, K. J. Fluorine Chem. 2004, 125, 1879. |
| [9] | (f) Doi, H.; Ban, I.; Nonoyama, A.; Sumi, K.; Kuang, C.; Hosoya, T.; Tsukada, H.; Suzuki, M. Chem. Eur. J. 2009, 15, 4165. |
| [9] | (g) Hu, J.; Gao, B.; Li, L.; Ni, C.; Hu, J. Org. Lett. 2015, 17, 3086. |
| [9] | (h) Ding, T.; Jiang, L.; Yang, J.; Xu, Y.; Wang, G.; Yi, W. Org. Lett. 2019, 21, 6025. |
| [10] | Prakash, G. K. S.; Ledneczki, I.; Chacko, S.; Olah, G. A. Org. Lett. 2008, 10, 557. |
| [11] | Nomura, Y.; Tokunaga, E.; Shibata, N. Angew. Chem., Int. Ed. 2011, 50, 1885. |
| [12] | Fujiwara, Y.; Dixon, J. A.; Hara, F.; Funder, E. D.; Dixon, D. D.; Rodriguez, R. A.; Baxter, R. D.; Herle, B.; Sach, N.; Collins, M. R.; Ishihara, Y.; Baran, P. S. Nature 2012, 492, 95. |
| [13] | (a) He, Z.; Tan, P.; Ni, C.; Hu, J. Org. Lett. 2015, 17, 1838. |
| [13] | (b) Shen, X.; Zhou, M.; Ni, C.; Zhang, W.; Hu, J. Chem. Sci. 2014, 5, 117. |
| [14] | Liu, Y.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2017, 56, 9930. |
/
| 〈 |
|
〉 |
