Cobalt-Catalyzed Divergent Aminofluorination and Diamination of Styrenes with N-Fluorosulfonamides.

作者: Ke-Yin Ye , Peng Guo , Jun-Fa Han , Jia-Bin Liao , Lin Chen

DOI: 10.1021/ACS.ORGLETT.1C01308

关键词:

摘要: A cobalt-catalyzed aminofluorination reaction of styrenes with N-fluorosulfonamides serving as both the amination and fluorination agents has been developed. The switch selectivity in this catalytic from to diamination could be easily achieved by addition 1.0 equiv PPh3. Both transformations tolerated a wide array substrates under mild conditions.

参考文章(57)
Thomas C Nugent, Chiral amine synthesis : methods, developments and applications Wiley-VCH Verlag GmbH & Co. KGaA. ,(2010) , 10.1002/9783527629541
Pinhong Chen, Guosheng Liu, Advancements in Aminofluorination of Alkenes and Alkynes: Convenient Access to β‐Fluoroamines European Journal of Organic Chemistry. ,vol. 2015, pp. 4295- 4309 ,(2015) , 10.1002/EJOC.201500231
S. N. Anderson, D. H. Ballard, J. Z. Chrzastowski, D. Dodd, M. D. Johnson, Inversion of configuration in the nucleophilic displacement of cobalt from alkylcobalt(IV) complexes and its relevance to the halogenation of the corresponding alkylcobalt(III) complexes Journal of The Chemical Society, Chemical Communications. pp. 685- 686 ,(1972) , 10.1039/C39720000685
E. G. Samsel, Jay K. Kochi, Radical chain mechanisms for alkyl rearrangement in organocobalt complexes Journal of the American Chemical Society. ,vol. 108, pp. 4790- 4804 ,(1986) , 10.1021/JA00276A017
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
Yingguang Zhu, Richard G. Cornwall, Haifeng Du, Baoguo Zhao, Yian Shi, Catalytic diamination of olefins via N-N bond activation. Accounts of Chemical Research. ,vol. 47, pp. 3665- 3678 ,(2014) , 10.1021/AR500344T
Shuifa Qiu, Tao Xu, Juan Zhou, Yinlong Guo, Guosheng Liu, Palladium-Catalyzed Intermolecular Aminofluorination of Styrenes Journal of the American Chemical Society. ,vol. 132, pp. 2856- 2857 ,(2010) , 10.1021/JA909716K
M.E. Vol'pin, I.Ya. Levitin, A.L. Sigan, A.T. Nikitaev, Current state of organocobalt(IV) and organorhodium(IV) chemistry Journal of Organometallic Chemistry. ,vol. 279, pp. 263- 280 ,(1985) , 10.1016/0022-328X(85)87024-8
Pier Alexandre Champagne, Justine Desroches, Jean-Denys Hamel, Mathilde Vandamme, Jean-François Paquin, Monofluorination of Organic Compounds: 10 Years of Innovation. Chemical Reviews. ,vol. 115, pp. 9073- 9174 ,(2015) , 10.1021/CR500706A
Sheldon S. Lande, Jay K. Kochi, Formation and oxidation of alkyl radicals by cobalt(III) complexes Journal of the American Chemical Society. ,vol. 90, pp. 5196- 5207 ,(1968) , 10.1021/JA01021A023