Stereoselective synthesis of α-fluoroacrylonitriles via organocatalytic cyanation of gem-difluoroalkenes and TMSCN
作者： Yu-Chuan Ma , Yang Zhang , Cheng-Zhi Gu , Guang-Fen Du , Lin He
DOI: 10.1039/C9NJ02370D
关键词: Selectivity 、 Cyanation 、 Trimethylsilyl cyanide 、 Nucleophile 、 Chemistry 、 Stereoselectivity 、 Medicinal chemistry 、 Catalysis
摘要: An organocatalytic cyanation reaction of gem-difluoroalkenes was developed. Under the catalysis 10 mol% DBU, undergo a nucleophilic addition-β-elimination with trimethylsilyl cyanide to provide α-fluoroacrylonitriles in 50–98% yields excellent Z/E selectivity.
rsc.org
sci-hub.se 参考文章(54)
Xiaoqiang Huang, Xinyao Li, Ning Jiao, Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation Chemical Science. ,vol. 6, pp. 6355- 6360 ,(2015) , 10.1039/C5SC02126J
Wei Su, Tian-Jun Gong, Bin Xiao, Yao Fu, Rhodium(III)-catalyzed cyanation of vinylic C–H bonds: N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent Chemical Communications. ,vol. 51, pp. 11848- 11851 ,(2015) , 10.1039/C4CC09790D
Said Eddarir, Mohammed Kajjout, Christian Rolando, Stereoselective cyanation of β-bromo-β-fluorostyrenes using potassium cyanide and promoted by (CH3CN)4Cu+ BF4− Tetrahedron. ,vol. 68, pp. 603- 607 ,(2012) , 10.1016/J.TET.2011.10.111
Satoshi Osada, Satoshi Sano, Mariko Ueyama, Yoshiro Chuman, Hiroaki Kodama, Kazuyasu Sakaguchi, Fluoroalkene modification of mercaptoacetamide-based histone deacetylase inhibitors. Bioorganic & Medicinal Chemistry. ,vol. 18, pp. 605- 611 ,(2010) , 10.1016/J.BMC.2009.12.005
Tomoya Fujiwara, David O’Hagan, Successful fluorine-containing herbicide agrochemicals Journal of Fluorine Chemistry. ,vol. 167, pp. 16- 29 ,(2014) , 10.1016/J.JFLUCHEM.2014.06.014
Alexandre Pradal, Gwilherm Evano, A vinylic Rosenmund-von Braun reaction: practical synthesis of acrylonitriles. Chemical Communications. ,vol. 50, pp. 11907- 11910 ,(2014) , 10.1039/C4CC05557H
Anthony J. Arduengo, Roland Krafczyk, Reinhard Schmutzler, Hugh A. Craig, Jens R. Goerlich, William J. Marshall, Markus Unverzagt, Imidazolylidenes, imidazolinylidenes and imidazolidines Tetrahedron. ,vol. 55, pp. 14523- 14534 ,(1999) , 10.1016/S0040-4020(99)00927-8
Grégory Landelle, Maxime Bergeron, Marc-Olivier Turcotte-Savard, Jean-François Paquin, Synthetic approaches to monofluoroalkenes Chemical Society Reviews. ,vol. 40, pp. 2867- 2908 ,(2011) , 10.1039/C0CS00201A
Shigeru Arai, Takashi Sato, Yuka Koike, Michino Hayashi, Atsushi Nishida, Palladium-catalyzed cyanation of carbon-carbon triple bonds under aerobic conditions. Angewandte Chemie. ,vol. 48, pp. 4528- 4531 ,(2009) , 10.1002/ANIE.200900030
Lin He, Hao Guo, Ying Wang, Guang-Fen Du, Bin Dai, N-heterocyclic carbene-mediated transformations of silicon reagents Tetrahedron Letters. ,vol. 56, pp. 972- 980 ,(2015) , 10.1016/J.TETLET.2015.01.034