Silver‐Assisted Difunctionalization of Terminal Alkynes: Highly Regio‐ and Stereoselective Synthesis of Bromofluoroalkenes

作者: Yibiao Li , Xiaohang Liu , Deyun Ma , Bifu Liu , Huanfeng Jiang

DOI: 10.1002/ADSC.201200250

关键词: ChemistryHalideCombinatorial chemistryReactivity (chemistry)RegioselectivitySilver fluorideMoietyOrganic chemistryVinyl fluorideReagentTriple bond

摘要: The difunctionalization of terminal alkynes was achieved with silver fluoride (AgF) and N-bromosuccinimide (NBS) as halogen sources. presence the halide moiety greatly enhances reactivity vinyl compounds that can probably be transformed into various products are difficult or even impossible to obtain via direct fluorination. Meanwhile, monofluoro alkenes were facilely synthesized a highly chemo- regioselective fluorination electron-deficient CC triple bonds using AgF fluorinating reagent in good yields.

参考文章(67)
Hui Xu, Shaojin Gu, Wanzhi Chen, Dacheng Li, Jianmin Dou, TBAF-mediated reactions of 1,1-dibromo-1-alkenes with thiols and amines and regioselective synthesis of 1,2-heterodisubstituted alkenes. Journal of Organic Chemistry. ,vol. 76, pp. 2448- 2458 ,(2011) , 10.1021/JO2000176
William S. Johnson, Balan Chenera, Fook S. Tham, Rudolph K. Kullnig, Cation-stabilizing auxiliaries in polyene cyclizations. 4. The fluorine atom as a cation-stabilizing auxiliary in biomimetic polyene cyclizations. 1. Background and exploratory experiments Journal of the American Chemical Society. ,vol. 115, pp. 493- 497 ,(1993) , 10.1021/JA00055A019
Bo Xu, Weibo Wang, Le-Ping Liu, Junbin Han, Zhuang Jin, Gerald B. Hammond, Synthetic evolutions in the nucleophilic addition to alkynes Journal of Organometallic Chemistry. ,vol. 696, pp. 269- 276 ,(2011) , 10.1016/J.JORGANCHEM.2010.09.025
Haihui Peng, Guosheng Liu, Palladium-catalyzed tandem fluorination and cyclization of enynes. Organic Letters. ,vol. 13, pp. 772- 775 ,(2011) , 10.1021/OL103039X
Grégory Landelle, Pier Alexandre Champagne, Xavier Barbeau, Jean-François Paquin, Stereocontrolled approach to bromofluoroalkenes and their use for the synthesis of tri- and tetrasubstituted fluoroalkenes. Organic Letters. ,vol. 11, pp. 681- 684 ,(2009) , 10.1021/OL8027412
Masanori Yoshida, Shuhei Yoshikawa, Tsuyoshi Fukuhara, Norihiko Yoneda, Shoji Hara, Stereoselective synthesis of (E)-1-fluoro-1,3-enynes Tetrahedron. ,vol. 57, pp. 7143- 7148 ,(2001) , 10.1016/S0040-4020(01)00683-4
Marie Schuler, Franck Silva, Carla Bobbio, Arnaud Tessier, Véronique Gouverneur, Gold(I)-catalyzed alkoxyhalogenation of beta-hydroxy-alpha,alpha-difluoroynones. Angewandte Chemie. ,vol. 47, pp. 7927- 7930 ,(2008) , 10.1002/ANIE.200802162
Alain Gorgues, Dominique Stéphan, Jack Cousseau, Mono-hydrofluorination of electrophilic alkynes by the liquid biphasic CsF–H2O–DMF system (DMF = N,N-dimethylformamide) J. Chem. Soc., Chem. Commun.. pp. 1493- 1494 ,(1989) , 10.1039/C39890001493
Xue-Yuan Liu, Pin Gao, Yong-Wen Shen, Yong-Min Liang, Copper‐Catalyzed Chloroamination of Alkynes: Highly Regio‐ and Stereoselective Synthesis of (E)‐β‐Chloro‐Enesulfonamides Advanced Synthesis & Catalysis. ,vol. 353, pp. 3157- 3160 ,(2011) , 10.1002/ADSC.201100382