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Published on: April 19, 2019
Perfluoroalkyl Aziridines with Ruthenium Porphyrin Carbene Intermediates
Kai Wu1, Cong-Ying Zhou1, Chi-Ming Che1
1State Key Laboratory of Synthetic Chemistry and Department of Chemistry , The University of Hong Kong, Hong Kong and HKU Shenzhen Institute of Research & Innovation , Shenzhen 518053 , China.
Abstract:
A new and efficient synthesis of multifunctionalized perfluoroalkyl aziridines via a ruthenium-perfluoroalkylcarbene intermediate is described. With Ru( p-Cl-TPP)CO as the catalyst, in situ generated C nF2 n+1CHN2 from C nF2 n+1CH2NH3Cl underwent a cascade of nitrone formation/1,3-diploar cycloaddition/rearrangement reactions with nitrosoarenes and alkynes to give a variety of multifunctionalized perfluoroalkyl aziridines in good to high yields and with moderate to high diastereoselectivity. The ruthenium-perfluoroalkylcarbene intermediates obtained through the stoichiometric reaction of ruthenium porphyrin and C nF2 n+1CHN2 were spectroscopically characterized.
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