三价磷化合物与亲电氟化试剂Selectfluor的氟化反应
收稿日期: 2017-04-01
修回日期: 2017-05-10
网络出版日期: 2017-06-02
基金资助
广东省科技计划（No.2015A020211026）、广东工业大学青年百人计划（No.220413506）和广东省功能分子工程重点实验室（No.2016kf07）资助项目.
Fluorination Reaction of P(Ⅲ) Compounds with the Electrophilic Fluorinating Reagent Selectfluor
Received date: 2017-04-01
Revised date: 2017-05-10
Online published: 2017-06-02
Supported by
Project supported by the Science and Technology Planning Project of Guangdong Province (No.2015A020211026),the 100 Young Talents Program of Guangdong University of Technology (No.220413506) and the Open Fund of the Key Laboratory of Functional Molecular Engineering of Guangdong Province (No.2016kf07).
黄昱霖 , 陈迁 . 三价磷化合物与亲电氟化试剂Selectfluor的氟化反应[J]. 有机化学, 2017 , 37(10) : 2745 -2751 . DOI: 10.6023/cjoc201704001
A fluorination reaction of P(Ⅲ) compounds with the electrophilic fluorinating reagent Selectfluor is described. The reaction proceeded in acetonitrile/water at room temperature for 15~60 min to afford phosphoric fluorides in 34%~81% yields.
[1] (a) Kosolapoff, G. M.; Maier, L. Organic Phosphorus Compounds, Wiley-Interscience, New York, 1972.
(b) Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415.
(c) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
(d) Tang, Q.; Tu, A. P.; Deng, Z. Z.; Hu, M. Y.; Zhong, W. H. Chin. J. Org. Chem. 2013, 33, 954(in Chinese). (唐谦, 涂爱平, 邓真真, 胡梦莹, 钟为慧, 有机化学, 2013, 33, 954.)
[2] (a) Steininger, H.; Schuster, M.; Kreuer, K. D.; Kaltbeitzel, A.; Bingol, B.; Meyer, W. H.; Schauff, S.; Brunklaus, G.; Maier, J.; Spiess, H. W. Phys. Chem. Chem. Phys. 2007, 9, 1764.
(b) Spampinato, V.; Tuccitto, N.; Quici, S.; Calabrese, V.; Marletta, G.; Torrisi, A.; Licciardello, A. Langmuir 2010, 26, 8400.
[3] (a) Shie, J.-J.; Fang, J.-M.; Wang, S.-Y.; Tsai, K.-C.; Cheng, Y.-S. E.; Yang, A.-S.; Hsiao, S.-C.; Su, C.-Y.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 11892.
(b) Shie, J.; Fang, J.; Wong, C. Angew. Chem. 2008, 120, 5872; Angew. Chem., Int. Ed. 2008, 47, 5788.
(c) Wydysh, E. A.; Medghalchi, S. M.; Vadlamudi, A.; Townsend, C. A. J. Med. Chem. 2009, 52, 3317.
[4] (a) Pinault, N. Coord. Chem. Rev. 2003, 241, 1.
(b) Knappke, C. E. I.; von Wangelin, A. J. Chem. Soc. Rev. 2011, 40, 4948.
(c) Fernández-Pérez, H.; Etayo, P.; Panossian, A.; Vidal-Ferran, A. Chem. Rev. 2011, 111, 2119.
[5] (a) Cho, C.-S.; Chen, L.-W.; Chiu, Y.-S. Polym. Bull. 1998, 41, 45.
(b) Cho, C.-S.; Fu, S.-C.; Chen, L.-W.; Wu, T.-R. Polym. Int. 1998, 47, 203.
[6] (a) Engel, R. Chem. Rev. 1977, 77, 349.
(b) Camps, F.; Coll, J.; Fabrias, G.; Guerrero, A. Tetrahedron 1984, 40, 2871.
(c) Sikder, A. K.; Pandey, K. S.; Jaiswal, D. K.; Dube, S. N.; Kumar, D.; Husain, K.; Bhattacharya, R.; Das Gupta, S. J. Pharm. Pharmacol. 1992, 44, 1038.
(d) Sikder, A. K.; Ghosh, A. K.; Jaiswal, D. K. J. Pharm. Sci. 1993, 82, 258.
(e) Eyer, P. Toxicol. Rev. 2003, 22, 165.
(f) Kim, T. H.; Oh, K. A.; Park, N. J.; Park, N. S.; Kim, Y. J.; Yum, E. K.; Jung, Y. S. J. Appl. Biomed. 2006, 4, 67.
[7] (a) Michalski, J.; Lopusinski, A. Angew. Chem., Int. Ed. 1982, 21, 294.
(b) Dabkowski, W.; Michalski, J. J. Chem. Soc., Chem. Commun. 1987, 755.
(c) Lermontov, S. A.; Popov, A. V.; Zavorin, S. I.; Sukhojenko, I. I.; Kuryleva, N. V.; Martynov, I. V.; Zefirov, N. S.; Stang, P. J. Fluorine Chem. 1994, 66, 233.
(d) Farooq, O. J. Chem. Soc., Perkin Trans. 11998, 839.
(e) Wozniak, L. A.; Chworos, A.; Pyzowski, L. A. Tetrahedron Lett. 1999, 40, 9337.
(f) Gololobov, Y. G.; Krasnova, I. Y.; Matveeva, E. V.; Petrovskii, P. V. Russ. Chem. Bull., Int. Ed. 2010, 59, 1059.
[8] (a) Kaushik, M. P.; Gupta, A. K.; Acharya, J.; Dubey, D. K. J. Fluorine Chem. 2008, 129, 226.
(b) Dubey, D. K.; Gupta, A. K.; Acharya, J.; Pardasani, D. Tetrahedron Lett. 2008, 49, 2232.
(c) Purohit, A. K.; Pardasani, D.; Kumar, A.; Goud, D. R.; Jain, R.; Dubey, D. K. Tetrahedron Lett. 2015, 56, 4593.
[9] Liu, N.; Mao, L.-L.; Yang, B.; Yang, S.-D. Chem. Commun. 2014, 50, 10879.
[10] Chen, Q.; Zeng, J.; Yan, X.; Huang, Y.; Wen, C.; Liu, X.; Zhang, K. J. Org. Chem. 2016, 81, 10043.
[11] Chen, Q.; Zeng, J.; Yan, X.; Huang, Y.; Du, Z.; Zhang, K.; Wen, C. Tetrahedron Lett. 2016, 57, 3379.
[12] Reddy, G. S.; Schmutzler, R. Z. Naturforsch. B 1970, 25, 1199.
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