Study on the Degradation of the Highly Reactive Hypervalent Trifluoromethylation Iodine Reagent PhI(OAc)(CF3)
Hui Zhu
Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China
National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorShusheng Zhang
National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorHaoyang Wang
National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Bin Xu
Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China
Bin Xu, Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China, Tel.: 0086-021-66132830
Yinlong Guo, National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-21-54925300
Search for more papers by this authorCorresponding Author
Yinlong Guo
National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Bin Xu, Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China, Tel.: 0086-021-66132830
Yinlong Guo, National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-21-54925300
Search for more papers by this authorHui Zhu
Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China
National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorShusheng Zhang
National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorHaoyang Wang
National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Bin Xu
Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China
Bin Xu, Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China, Tel.: 0086-021-66132830
Yinlong Guo, National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-21-54925300
Search for more papers by this authorCorresponding Author
Yinlong Guo
National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Bin Xu, Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China, Tel.: 0086-021-66132830
Yinlong Guo, National Center for Organic Mass Spectrometry in Shanghai, State Key Laboratory of Organmetallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-21-54925300
Search for more papers by this authorAbstract
Degradation of the highly reactive hypervalent trifluoromethylation iodine reagent PhI(OAc)(CF3), which can only be generated in situ with mixing PhI(OAc)2 and TMSCF3 in the presence of CsF, was studied by ESI-MS and GC-MS combined with 19F-NMR. The important transient intermediate PhICF3+ was determined by ESI-MS, and the major volatile products containing CF3 were identified with the authentic compounds by using GC-MS, such as trifluoromethylbenzene, 2-iodobenzotrifluoride, 3-iodobenzotrifluoride, 4-iodobenzotrifluoride. Meanwhile, more evidences obtained with 19F-NMR were given for such degradation reaction. A possible rapid CF3 radical transfer reaction pathway was proposed to clarify such degradation progress based on the experimental results. Therefore, this study may be helpful in elucidating the intrinsic reactivity of PhI(OAc)(CF3) and the possible competing side reactions caused by such self-degradation pathway.
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