Electrolyte-free electrochemical C–H trifluoromethylation of 2-pyridones under batch and flow conditions

Abstract

Herein, we report, a direct C3 trifluoromethylation of 2-pyridones including unprotected derivatives by an electrochemical approach using the readily available Langlois’s reagent as the CF3 source in the absence of...

Catalyst‐ and Oxidant‐Free Electrochemical Regioselective Halogenation and Trifluoromethylation of 4H‐Pyrido[1,2‐a]pyrimidin‐4‐ones

“…Based on these results and previous reports, [9f,13c–f,14] a possible mechanism for the electrochemical oxidative radical chlorination and trifluoromethylation of 4 H ‐pyrido[1,2‐ a ]pyrimidin‐4‐one is illustrated in Scheme 3. Initially, the Cl − or SO 2 CF 3 − at the anode was first oxidized to generate Cl or CF 3 radical, which attacked the C3 position of 2‐phenyl‐4 H ‐pyrido[1,2‐ a ]pyrimidin‐4‐one 1 a to form radical intermediate A .…”

Supporting Electrolyte‐Free Electrochemical Oxidative C−H Sulfonylation and Thiocyanation of Fused Pyrimidin‐4‐Ones in an All‐Green Electrolytic System

“…[a] leading to a waste of resources and ultimately reducing the overall yield. [21] Moreover, there may be an issue with the solubility of the electrolytes. Replacing 2 a with other sulfonylcontaining reagents such as p-tolylsulfinic acid, benzenesulfonyl hydrazide, or p-toluenesulfonyl chloride delivered 3 a in only poor yields (entry 11).…”

Electrocatalytic synthesis: an environmentally benign alternative for radical-mediated aryl/alkenyl C(sp2)–C(sp3) cross-coupling reactions

“…These radicals then attack the glycal double bond to deliver the carbon-centered radical II, which is further oxidized into the carbocation intermediate III. 54 In addition, this synthetic strategy not only retained the advantages of being metal-, oxidant-, and electrolyte-free but also achieved C(sp 2 )-H trifluoromethylation under microfluidic conditions. A comprehensive survey of the substrate scope and reaction conditions showed that a microflow electrocell (600 μL, 12 cm 2 surface area) was beneficial for improving the reaction selectivity and prevented the undesired partial degradation of certain sensitive products.…”