Photoredox Trifluoromethylation/Cyclization of N-Arylacrylamides with 4-(Difluoroamino)-1-[(trifluoromethyl)sulfonyl]pyridinium Triflate (TFSP)

Abstract

Photoredox trifluoromethylation/cyclization of N-arylacrylamides with inexpensive and stable solid trifluoromethylsulfonyl−pyridinium salt (TFSP) have been developed.

Visible-light-induced self-catalyzed fluoroalkylation/cyclization of N-arylcinnamamides: synthesis of fluoroalkyl-containing 3,4-disubstituted dihydro-1,5-naphthyridin-2(1H)-ones and 7,8-disubstituted dihydropyrido[3,2-d]pyrimidin-6(5H)-ones

“…Over the past decade, radical fluoroalkylation/cyclization tandems have emerged as efficient approaches for constructing fluoroalkyl-containing aromatic heterocycles, contributing significantly to advancements in the field. 5 Notably, Mai et al reported a radical trifluoromethylation/cyclization tandem of N -arylcinnamamides utilizing Langlois’ reagent as the trifluoromethyl source, K 2 S 2 O 8 as the oxidant, and AgNO 3 as the catalyst, resulting in the formation of trifluoromethylated dihydroquinolinones. 5 h Recently, Zang et al developed an electrochemical trifluoromethylation/cyclization cascade employing CuOTf as the mediator, and LiClO 4 as the electrolyte to synthesize trifluoromethylated tetrahydroquinolines and dihydroquinolinones.…”