One-Pot α-Nucleophilic Fluorination of Acetophenones by DBDMH and Et3N·3HF

doi:10.6023/cjoc1111261

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (06): 1146-1149.DOI: 10.6023/cjoc1111261 Previous Articles Next Articles

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使用DBDMH 和Et₃N·3HF 的苯乙酮一锅法α-亲核氟代

朱伟, 李忠洲, 姚璐璐, 郑祖彪, 邹新琢

华东师范大学化学系上海 200062

收稿日期:2011-11-26 修回日期:2011-12-23 发布日期:2012-02-04
通讯作者: 邹新琢 E-mail:xzzou@chem.ecnu.edu.cn

One-Pot α-Nucleophilic Fluorination of Acetophenones by DBDMH and Et₃N·3HF

Zhu Wei, Li Zhongzhou, Yao Lulu, Zheng Zubiao, Zou Xinzhuo

Department of Chemistry, East China Normal University, Shanghai 200062

Received:2011-11-26 Revised:2011-12-23 Published:2012-02-04

A novel synthetic method of α-fluoroacetophenones directly from acetophenones via one-pot reactions of bromination and fluorination is reported. Based on the nucleophilic fluorination, using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as brominating reagent, triethylamine tris(hydrogen fluoride) as fluorinating reagent, α-fluoroacetophenones were obtained from acetophenones in 82%～87% total yields, except p- and m-nitroacetophenones. The proposed method has a high application value, because of its simplicity, low cost and good yields.

Key words: α-nucleophilic fluorination, α-fluoroacetophenones, acetophenones, one-pot, Et₃N·3HF, 1,3-dibromo-5,5-dimethylhydantoin

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Zhu Wei, Li Zhongzhou, Yao Lulu, Zheng Zubiao, Zou Xinzhuo. One-Pot α-Nucleophilic Fluorination of Acetophenones by DBDMH and Et₃N·3HF[J]. Chin. J. Org. Chem., 2012, 32(06): 1146-1149.

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[1] Perutz, R. N. Science 2008, 321, 1168.

[2] Chen, Q.; Qiu, X.; Qing, F. J. Org. Chem. 2006, 71, 3762.

[3] Qian, J.; Cao, W.; Zhang, H.; Chen, J.; Zhu, S. J. Fluorine Chem.2007, 128, 207.

[4] Zheng, Z. B.; Li, X. J.; Wang, C. C.; Zou, X. Z. Chin. J. Org.Chem. 2011, 31, 1624 (in Chinese).(郑祖彪, 李新军, 王翠翠, 邹新琢, 有机化学, 2011, 31, 1624.)
[5] Li, M. R.; Cai, X. Q.; Zhu Y. F.; Liu, K. G.; Hu, M. L. Acta Chim.Sinica 2011, 69(4), 425 (in Chinese).(李美容, 蔡晓庆, 朱易峰, 刘宽冠, 胡茂林, 化学学报, 2011,69(4), 425.)
[6] Hou, H. F.; Chen, B. Y.; Zhang, X. S.; Wang, Z. Y. Acta Chim.Sinica 2011, 69(6), 617 (in Chinese).(侯海锋, 陈斌媛, 张学胜, 王遵尧, 化学学报, 2011, 69(6), 617.)
[7] Prakash, G. K. S.; Beier, P. Angew. Chem., Int. Ed. 2006, 45, 2172.

[8] Lawrence, N. J.; Patterson, R. P.; Ooi, L. L.; Cook, D.; Ducki, S.Bioorg. Med. Chem. Lett. 2006, 16, 5844.

[9] Lystvet, S. M.; Hoff, B. H.; Anthonsen, T.; Jacobsen, E. E. Biocatal.Biotransform. 2010, 28, 272.

[10] Thvedt, T. H. K.; Fuglseth, E.; Sundby, E.; Hoff, B. H. Tetrahedron2010, 66, 6733.

[11] Fuglseth, E.; Sundby, E.; Hoff, B. H. J. Fluorine Chem. 2009, 130,600.

[12] Katoch-Rouse, R.; Pavlova, O. A.; Caulder, T.; Hoffman, A. F.;Mukhin, A. G.; Horti, A. G. J. Med. Chem. 2003, 46, 642.

[13] Heinrich, M. R. Tetrahedron Lett. 2007, 48, 3895.

[14] Uneyama, K. Organofluorine Chemistry, Blackwell Press, UK,2006.
[15] Qing, F.; Qiu, X. Organofluorine Chemistry, Science Publishing,Beijing, 2007 (in Chinese).(卿凤翎, 邱小龙, 有机氟化学, 科学出版社, 北京, 2007.)
[16] Fuglseth, E.; Thvedt, T. H. K.; Moll, M. F.; Hoff, B. H. Tetrahedron2008, 64, 7318.

[17] Thvedt, T. H. K.; Fuglseth, E.; Sundby, E.; Hoff, B. H. Tetrahedron2009, 65, 9550.

[18] Stavber, G.; Zupan, M.; Stavber, S. Synlett 2009, 589.
[19] Chen, Z. Z.; Zhu, W.; Zheng, Z. B.; Zou, X. Z. J. Fluorine Chem.2010, 131, 340.

[20] Teresa, H.; Cristina, N. Chem. Commun. 2011, 47, 248.

[21] Arthurs, C. L.; Morris, G. A.; Piacenti, M.; Pritchard, R. G.; Stratford,I. J.; Tatic, T.; Whitehead, R. C.; Williams, K. F.; Wind, N. S.Tetrahedron 2010, 66, 9049.

[22] Loghmani, H.; Dariush, H. J. Fluorine Chem. 2010, 131, 561.

[23] Yamamoto, T.; Suzuki, Y.; Ito, E.; Tokunaga, E.; Shibata, N. Org.Lett. 2011, 13, 470.

[24] Stavber, G.; Zupan, M.; Stavber, S. Tetrahedron Lett. 2007, 48,2671.

[25] Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.

[26] Dai, X. J.; Wang, Y. P.; Zhao, S. Y. Chin. J. Org. Chem. 2009, 29,1307 (in Chinese).(戴希杰, 王亚平, 赵圣印, 有机化学, 2009, 29, 1307.)
[27] Gao, G. R.; Guan, X. X.; Zou, X. Z. Chin. J. Org. Chem. 2007, 27,109 (in Chinese).(高国锐, 管细霞, 邹新琢, 有机化学, 2007, 27, 109.)
[28] Chen, Z. Z.; Zhou, B.; Cai, H. H.; Zhu, W.; Zou, X. Z. GreenChem. 2009, 11, 275.

使用DBDMH 和Et₃N·3HF 的苯乙酮一锅法α-亲核氟代

One-Pot α-Nucleophilic Fluorination of Acetophenones by DBDMH and Et₃N·3HF

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使用DBDMH 和Et3N·3HF 的苯乙酮一锅法α-亲核氟代