Direct Photoredox‐Catalyzed Reductive Difluoromethylation of Electron‐Deficient Alkenes
作者： Xiao-Jun Tang , Zuxiao Zhang , William R. Dolbier
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摘要: Photoredox-catalyzed reductive difluoromethylation of electron-deficient alkenes was achieved in one step under tin-free, mild and neutral conditions. This protocol affords a facile method to introduce RCF2 (R=H, Ph, Me, CH2N3) groups at sites β electron-withdrawing groups. It found that TTMS (tris(trimethylsilyl)silane) served nicely as both the H-atom donor electron catalytic cycle. Experimental DFT computational results provided evidence Me) radicals are nucleophilic nature.
sci-hub.se 参考文章(64)
Christopher C. Nawrat, Christopher R. Jamison, Yuriy Slutskyy, David W. C. MacMillan, Larry E. Overman, Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling. Journal of the American Chemical Society. ,vol. 137, pp. 11270- 11273 ,(2015) , 10.1021/JACS.5B07678
Piotr Dudziński, Andrej V. Matsnev, Joseph S. Thrasher, Günter Haufe, Ambiphilic Properties of SF5CF2CF2Br Derived Perfluorinated Radical in Addition Reactions Across Carbon–Carbon Double Bonds Organic Letters. ,vol. 17, pp. 1078- 1081 ,(2015) , 10.1021/ACS.ORGLETT.5B00268
Xiang Chen, Zhiyong Yang, Ze Tan, Jidan Liu, Shaobo Zhuang, Qingwen Gui, Synthesis of Oxindoles through Silver‐Catalyzed Trifluoromethylation–, Difluoromethylation– and Arylsulfonylation–Cyclization Reaction of N‐Arylacrylamides European Journal of Organic Chemistry. ,vol. 2014, pp. 3196- 3202 ,(2014) , 10.1002/EJOC.201400087
Iwao Ojima, Fluorine in medicinal chemistry and chemical biology Wiley. ,(2009) , 10.1002/9781444312096
Qing-Yu Lin, Xiu-Hua Xu, Feng-Ling Qing, Visible light-induced selective hydrobromodifluoromethylation of alkenes with dibromodifluoromethane Organic and Biomolecular Chemistry. ,vol. 13, pp. 8740- 8749 ,(2015) , 10.1039/C5OB01302J
Ricardo A. Angnes, Zhou Li, Carlos Roque D. Correia, Gerald B. Hammond, Recent synthetic additions to the visible light photoredox catalysis toolbox. Organic and Biomolecular Chemistry. ,vol. 13, pp. 9152- 9167 ,(2015) , 10.1039/C5OB01349F
Tomoko Yajima, Kanako Yamaguchi, Rie Hirokane, Emiko Nogami, Photoinduced radical hydroperfluoroalkylation and the synthesis of fluorinated amino acids and peptides Journal of Fluorine Chemistry. ,vol. 150, pp. 1- 7 ,(2013) , 10.1016/J.JFLUCHEM.2013.02.019
Hanns Fischer, Leo Radom, Factors Controlling the Addition of Carbon-Centered Radicals to Alkenes—An Experimental and Theoretical Perspective Angewandte Chemie International Edition. ,vol. 40, pp. 1340- 1371 ,(2001) , 10.1002/1521-3773(20010417)40:8<1340::AID-ANIE1340>3.0.CO;2-#
Jian Chen, Chang-Ming Hu, Synthesis of functionalized compounds containing a difluoromethylene moiety Journal of the Chemical Society, Perkin Transactions 1. pp. 1111- 1114 ,(1994) , 10.1039/P19940001111
Roberto A. Rossi, Adriana B. Pierini, Alicia B. Peñéñory, Nucleophilic substitution reactions by electron transfer Chemical Reviews. ,vol. 103, pp. 71- 167 ,(2003) , 10.1021/CR960134O