Transition-metal-free visible-light photoredox catalysis at room-temperature for decarboxylative fluorination of aliphatic carboxylic acids by organic dyes

作者: Xinxin Wu , Chunna Meng , Xiaoqian Yuan , Xiaotong Jia , Xuhong Qian

DOI: 10.1039/C5CC04527D

关键词:

摘要: We report herein an efficient, general and green method for decarboxylative fluorination of aliphatic carboxylic acids. By using a transition-metal-free, organocatalytic photoredox system, the reaction various acids with Selectfluor reagent afforded corresponding alkyl fluorides in satisfactory yields under visible light irradiation at room temperature.

参考文章(62)
David A. Nagib, Mark E. Scott, David W. C. MacMillan, Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis Journal of the American Chemical Society. ,vol. 131, pp. 10875- 10877 ,(2009) , 10.1021/JA9053338
Jun Xuan, Xu-Dong Xia, Ting-Ting Zeng, Zhu-Jia Feng, Jia-Rong Chen, Liang-Qiu Lu, Wen-Jing Xiao, Visible‐Light‐Induced Formal [3+2] Cycloaddition for Pyrrole Synthesis under Metal‐Free Conditions Angewandte Chemie. ,vol. 53, pp. 5653- 5656 ,(2014) , 10.1002/ANIE.201400602
Montserrat Rueda-Becerril, Claire Chatalova Sazepin, Joe C. T. Leung, Tulin Okbinoglu, Pierre Kennepohl, Jean-François Paquin, Glenn M. Sammis, Fluorine Transfer to Alkyl Radicals Journal of the American Chemical Society. ,vol. 134, pp. 4026- 4029 ,(2012) , 10.1021/JA211679V
Carlo Cassani, Giulia Bergonzini, Carl-Johan Wallentin, Photocatalytic decarboxylative reduction of carboxylic acids and its application in asymmetric synthesis. Organic Letters. ,vol. 16, pp. 4228- 4231 ,(2014) , 10.1021/OL5019294
W. Liu, X. Huang, M.-J. Cheng, R. J. Nielsen, W. A. Goddard, J. T. Groves, Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin Science. ,vol. 337, pp. 1322- 1325 ,(2012) , 10.1126/SCIENCE.1222327
K. Muller, C. Faeh, F. Diederich, Fluorine in Pharmaceuticals: Looking Beyond Intuition. Science. ,vol. 317, pp. 1881- 1886 ,(2007) , 10.1126/SCIENCE.1131943
Timothy J. Barker, Dale L. Boger, Fe(III)/NaBH4-Mediated Free Radical Hydrofluorination of Unactivated Alkenes Journal of the American Chemical Society. ,vol. 134, pp. 13588- 13591 ,(2012) , 10.1021/JA3063716
D. M. Schultz, T. P. Yoon, Solar Synthesis: Prospects in Visible Light Photocatalysis Science. ,vol. 343, pp. 1239176- 1239176 ,(2014) , 10.1126/SCIENCE.1239176
Shunichi Fukuzumi, Hiroaki Kotani, Kei Ohkubo, Seiji Ogo, Nikolai V. Tkachenko, Helge Lemmetyinen, Electron-transfer state of 9-mesityl-10-methylacridinium ion with a much longer lifetime and higher energy than that of the natural photosynthetic reaction center. Journal of the American Chemical Society. ,vol. 126, pp. 1600- 1601 ,(2004) , 10.1021/JA038656Q