β,β-二氟乙烯基化合物制备方法研究进展

doi:10.6023/cjoc1104113

有机化学 ›› 2012, Vol. 32 ›› Issue (04): 661-666.DOI: 10.6023/cjoc1104113 上一篇下一篇

综述与进展

β,β-二氟乙烯基化合物制备方法研究进展

刘运, 邓萌萌, 张智勇, 丁肖华, 戴志群, 关金涛

武汉工业学院化学与环境工程学院武汉 430023

收稿日期:2011-04-11 修回日期:2011-09-19 发布日期:2012-04-24
通讯作者: 张智勇 E-mail:zzy6211@126.com, zzy6211@yahoo.com.cn
基金资助:
国家自然科学基金(No. 60736)、湖北省自然科学基金(No. 2007ABA279)、湖北省教育厅科技基金(No. Z0091801)、武汉工业学院研究生教育创新计划(No. 09cx19)资助项目.

Progress in Preparation of β,β-Difluorovinyl Compounds

Liu Yun, Deng Mengmeng, Zhang Zhiyong, Ding Xiaohua, Dai Zhiqun, Guan Jintao

Department of Chemistry and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023

Received:2011-04-11 Revised:2011-09-19 Published:2012-04-24
Supported by:
Project supported by the National Natural Science Foundation of China (No. 60736), the Natural Science Foundation of Hubei Province of China (No. 2007ABA279), the Scientific Research Fund of Hubei Provincial Education Department (No. Z0091801), and the Educational and Innovative Foundation for the Graduate Students of Wuhan Polytechnic University (No. 09cx19).

文章分享

摘要/Abstract

近年来, 随着β,β-二氟乙烯基类化合物的广泛应用, 其合成方法的研究也越来越多. 详细介绍了卤代二氟醋酸盐、卤代二氟甲烷、双膦酸盐、有金属参与、双三氟甲基汞和二异丙基胺基锂和二氟甲基芳环砜等法制备β,β-二氟乙烯的研究进展, 同时对其反应机理作了相应阐述.

关键词: 二氟乙烯, Wittig 反应, 磷叶立德

Numerous methods for the preparation of β,β-difluorovinyl compounds have been reported with the widely application of difluoroethenes recently. In this paper, an overview on the progress of synthetic methods of β,β-difluorovinyl compounds, based on halodifluroacetate, halodifluoromethane, bi-sphosphonium salts, metal-assisted, double-trifluoromethyl mercury, LDA and difluormethyl aromatic sulfone, has been introduced. And the relevant reaction mechanisms are also proposed and explained.

Key words: difluoroethylene, Wittig reaction, phosphorus ylide

引用此文

刘运, 邓萌萌, 张智勇, 丁肖华, 戴志群, 关金涛. β,β-二氟乙烯基化合物制备方法研究进展[J]. 有机化学, 2012, 32(04): 661-666.

Liu Yun, Deng Mengmeng, Zhang Zhiyong, Ding Xiaohua, Dai Zhiqun, Guan Jintao. Progress in Preparation of β,β-Difluorovinyl Compounds[J]. Chin. J. Org. Chem., 2012, 32(04): 661-666.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Wittig, G. V.; Geissler, G. Justus Liebigs Ann. Chem. 1953, 580, 44.

[2] Pommer, H. Angew. Chem., Int. Ed. Engl. 1977, 16, 423.

[3] Franzen, V. Chem. Ber. 1962, 95, 1964.

[4] Tozer, J.; Herpin, F. Tetrahedron 1996, 52, 8619.

[5] Nenajdenko, G.; Varseev, N.; Korotchenko, N.; Shastin, V.; Balenkova, S. J. Fluorine Chem. 2003, 124, 115.

[6] Naae, G.; Burton, J. Synth. Commun. 1973, 3, 197.

[7] Hayashi, S.; Nakai, T.; Ishikawa, N.; Burton, J.; Naae, G.; Kesling, S. Chem. Lett. 1979, 983.

[8] Kitano, K.; Makoto, U.; Manabu, U.; Suzuki, T. EP 325796, 1989[Chem. Abstr. 1989, 112, 46254].

[9] Rieger, B.; Reiffenrath, V.; Hittich, R. DE 4018651, 1991 [Chem. Abstr. 1991, 117, 122050].

[10] Pauluth, D.; Frinkenzeller, U. DE 4314085, 1994 [Chem. Abstr. 1994, 122, 80863].

[11] Takashi, K.; Shuichi, M.; Hiroyuki, T.; Yasuhiro, K.; Nakagawa, E.EP 1170352, 2002 [Chem. Abstr. 2002, 136, 110195].

[12] Nguyen, V.; Burton, J. J. Org. Chem. 1997, 62, 7758.

[13] Kazuaki, T.; Andreas, B.; Eike, P. DE 19650634, 1998 [Chem. Abstr. 1998, 129, 60629].

[14] Ekkehard, B.; Herber, D.; Eidenschink, M. WO 9221734, 1992[Chem. Abstr. 1992, 120, 285950].

[15] Bremer, M.; Pauluth, D.; Heckmeier, M.; Duebal H.-R.; Hornung, B.; Schmidt, W.; Wingen, R. DE 10225048, 2002 [Chem. Abstr. 2002, 138, 31093].

[16] Yasuhiro, H.; Masayuki, S. EP 2028252, 2009 [Chem. Abstr. 2009, 150, 249656].

[17] Haseba, Y.; Matsui, S.; Takeuchi, H.; Kubo, Y.; Nakagawa, E. JP 2001328975, 2001 [Chem. Abstr. 2001, 136, 12960]

[18] (a) Saito, M.; Kibe, S. WO 2009028367, 2009 [Chem. Abstr. 2009, 150, 272229]. (b) Saito, M.; Kibe, S. WO 2009028368, 2009 [Chem. Abstr. 2009, 150, 272226].

[19] Haseboa, Y.; Saito, M. EP 2028252, 2009 [Chem. Abstr. 2009, 150, 249656].

[20] Faqua, A.; Duncan, G.; Silverstein, M. Tetrahedron Lett. 1964, 5, 1461.

[21] Fuqua, A.; Duncan, G.; Silverstein, M. J. Org. Chem. 1965, 30, 1027.

[22] Fuqua, A.; Duncan, G.; Silverstein, M. Tetrahedron Lett. 1965, 6, 521.

[23] Fuqua, A.; Duncan, G.; Silverstein, M. J. Org. Chem. 1965, 30, 2543.

[24] Herkes, E.; Burton, J. J. Org. Chem. 1967, 32, 1311.

[25] Kitano, K. EP 0377469, 1990 [Chem. Abstr. 1990, 114, 53382].

[26] (a) Wheaton G. A.; Burton, D. J. J. Org. Chem. 1983, 48, 917. (b) Burton, D. J.; Yang, Z.-Y.; Qiu, W.-M. Chem. Rev. 1996, 96, 1641.

[27] Robert, R. US 3225106, 1965 [Chem. Abstr. 1965, 64, 43505].

[28] Naae, G.; Burton, D. J. J. Fluorine Chem. 1971, 1, 123.

[29] Naae, G.; Burton, D. J. Synth. Commun. 1973, 3, 197.

[30] Ueki, H.; Chiba, T.; Yamazaki, T. J. Org. Chem. 2004, 69, 7616.

[31] Kesling, S. Ph.D. Dissertation, University of Iowa, Iowa, 1975.

[32] Burton, J.; Kesling, S.; Naae, G. J. Fluorine Chem. 1981, 18, 293.

[33] Richard, P.; Portella, C. Carbohydr. Res. 2000, 327, 119.

[34] Suda, M. Tetrahedron Lett. 1981, 22, 1421.

[35] Bhadury, S.; Palit, M.; Sharma, M.; Raza, K.; Jaiswal, K. J. Fluorine Chem. 2002, 116, 75.

[36] Motherwell, B.; Tozer, J.; Ross, C. J. Chem. Soc., Chem. Commun. 1989, 1437.

[37] Houlton, S.; Motherwell, B.; Tozer, J.; Ross, C. Tetrahedron 1993, 49, 8087.

[38] Nowak, I.; Robins, M. J. Org. Lett. 2005, 7, 721.

[39] (a) Raghavanpillai A.; Burton, D. J. Tetrahedron Lett. 2002, 43, 2731. (b) Raghavanpillai A.; Burton, D. J. J. Org. Chem. 2004, 69, 7083. (c) Raghavanpillai A.; Burton, D. J. J. Fluorine Chem. 2005, 126, 833. (d) Raghavanpillai A.; Burton, D. J. J. Org. Chem. 2006, 71, 194.

[40] Zibinsky, M.; Beier, P.; Prakash, S. Chem. Sust. Dev. 2008, 16, 69.

[41] Prakash G. K. S.; Wang Y.; Hu, J.-B.; Olah, G. A. J. Fluorine Chem. 2005, 126, 1361.

[42] Zhao, Y.-C.; Huang, W.-Z.; Zhu L.-G.; Hu, J.-B. Org. Lett. 2010, 12, 1444.

[43] Zhu, L.-G.; Li, Y.; Zhao, Y.-C.; Hu, J.-B. Tetrahedron Lett. 2010, 51, 6150.

β,β-二氟乙烯基化合物制备方法研究进展

Progress in Preparation of β,β-Difluorovinyl Compounds

PDF

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 8

编辑推荐

相关统计

本文评价

[1]	曹成瑶, 牛亚茹, 蒋昀辰, 曲红梅, 陈超. 钯催化的氯二氟乙基高价碘试剂对于乙酰苯胺C—H键的氯二氟乙基化反应研究[J]. 有机化学, 2022, 42(7): 2098-2105.
[2]	马献涛, 于静, 马瑞甜, 燕然, 张振雷. 钯催化下稳定磷叶立德与烯丙基醇的脱水偶联反应[J]. 有机化学, 2019, 39(3): 830-835.
[3]	徐四龙, 贺峥杰. 烯丙基磷叶立德与羰基化合物的Vinylogous类型有机反应研究进展[J]. 有机化学, 2014, 34(12): 2438-2447.
[4]	李小六, 魏思楠, 张宏波, 张平竹, 王玮, 陈华. 含醛基及叠氮基氮杂糖中间体的合成[J]. 有机化学, 2012, 32(9): 1708-1714.
[5]	徐四龙, 贺峥杰. 原位生成的烯丙基磷叶立德与醛的化学反应性研究[J]. 有机化学, 2012, 32(07): 1159-1168.
[6]	陈莉, 孙绍发, 宋功武. 顺序一锅法合成5,6,8-三氢-吡喃并[3',4':4,5]噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物[J]. 有机化学, 2012, 32(07): 1314-1318.
[7]	闾新明, 钱鹰. 新型超支化荧光聚合物的合成及光物理性质[J]. 有机化学, 2011, 31(01): 82-86.
[8]	王宏青, 刘惠, 刘钊杰. 吡唑并嘧啶氧苯氧乙酸酯类化合物的合成与除草活性[J]. 有机化学, 2004, 24(12): 1563-1568.