Chinese Journal of Organic Chemistry >
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).
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.
Huang Yulin , Chen Qian . Fluorination Reaction of P(Ⅲ) Compounds with the Electrophilic Fluorinating Reagent Selectfluor[J]. Chinese Journal of Organic Chemistry, 2017 , 37(10) : 2745 -2751 . DOI: 10.6023/cjoc201704001
[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.
/
| 〈 |
|
〉 |