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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Rhenium(I)-Catalyzed ortho-C-H Addition to Bicyclic Alkenes
Sekar Prakash1, Yu-Che Chang1, Chien-Hong Cheng1
1Department of Chemistry, National Tsing Hua University, Hsinchu, 30013, Taiwan.
Abstract:
Hydroarylation of bicyclic alkenes has been developed using a low-valent ReI -catalyzed, directing group-assisted C-H bond activation strategy. The addition of sodium acetate significantly improves the reaction efficiency; moreover, bicyclic alkenes such as 7-oxa and aza benzonorbornadienes worked efficiently under this reaction condition. Preliminary mechanistic studies suggest that, after the alkene insertion, the rhenacycle preferentially undergoes protonolysis rather than reductive elimination.
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