Direct alkylation of quinoxalinones with electron-deficient alkenes enabled by a sequential paired electrolysis

Abstract

The unprecedented alkylation of quinoxalinones with electron-deficient alkenes has been realized by a sequential paired electrolysis.

Electrophotoredox cerium-catalyzed decarboxylative radical cyclization cascade for the synthesis of alkylated benzimidazo-fused isoquinolinones

“…36 However, the primary C(sp 3 )–H bonds failed to work, while the tertiary C(sp 3 )–H bonds were limited to adamantanes but with low regioselectivities. To address these challenges, and in continuation of our interest in organic electrosynthesis, 37–41 we rationalized that the use of aliphatic carboxylic acids as the radical precursors would provide an appealing solution, since the decarboxylation process allows the generation of various alkyl radicals with excellent site-selectivities. In this context, Yu and co-workers have reported a AgNO 3 /K 2 S 2 O 8 -mediated decarboxylative radical cyclization cascade for the synthesis of alkylated benzimidazo-fused isoquinolinones.…”

Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF3+OTf–) as a Bifunctional Reagent

“…Alternatively, the addition of mediators to shift one of the half reactions from heterogeneous to homogeneous form is also a reliable strategy to run a paired electrolysis (Scheme a) . Due to our continued interests in paired electrolysis, we questioned if the mediator could be integrated with radical precursors to form bifunctional molecules (Scheme b). Taking a consecutive paired electrolysis for example, the reduction of bifunctional molecule (Y-LG) I generates radical II and a leaving group III .…”