885-94-9Relevant articles and documents
Addition Reaction of Immonium Benzotriazolates To Acetylenic Esters
Katritzky, Alan R.,Fali, Clara N.,Oniciu, Daniela C.
, p. 1069 - 1076 (1995)
1-Dialkylaminomethylbenzotriazoles react with ethyl propiolate and dimethyl acetylenedicarboxylate by addition of the benzotriazole anion followed by the immonium cation.The benzotriazolyl group in the products undergoes facile nucleophilic displacement.
Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants
Targos, Karina,Williams, Oliver P.,Wickens, Zachary K.
, p. 4125 - 4132 (2021/04/07)
We describe a photocatalytic system that reveals latent photooxidant behavior from one of the most reducing conventional photoredox catalysts, N-phenylphenothiazine (PTH). This aerobic photochemical reaction engages difficult to oxidize feedstocks, such as benzene, in C(sp2)-N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and with Lewis acid cocatalysts scavenging inhibitors inextricably formed in this process.
Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication
Huang, He,Strater, Zack M.,Rauch, Michael,Shee, James,Sisto, Thomas J.,Nuckolls, Colin,Lambert, Tristan H.
supporting information, p. 13318 - 13322 (2019/08/12)
Visible-light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron transfer (SET), resulting in C?H/N?H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the cis-2,6-dimethylpiperidine moieties.