He Huang1, Zack M Strater2, Tristan H Lambert1,2. 1. Department of Chemistry and Chemical Biology , Cornell University , Ithaca , New York 14853 , United States. 2. Department of Chemistry , Columbia University , New York , New York 10027 , United States.
Abstract
The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.
The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a n class="Chemical">trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.
Authors: Ian B Perry; Thomas F Brewer; Patrick J Sarver; Danielle M Schultz; Daniel A DiRocco; David W C MacMillan Journal: Nature Date: 2018-08-01 Impact factor: 49.962