Photoredox Catalysis Enables Decarboxylative Cyclization with Hypervalent Iodine(III) Reagents: Access to 2,5-Disubstituted 1,3,4-Oxadiazoles

The cyanation and formylation of imidazo[1,2-a]pyridines were developed under copper-mediated oxidative conditions using ammonium iodide and DMF as a nontoxic combined cyano-group source and DMF as a formylation reagent. Mechanistic studies indicate that the cyanation of imidazo[1,2-a]pyridines proceeds through a two-step sequence: initial iodination and then cyanation. The cyanation has a broad substrate scope and high functional group tolerance, and can be safely conducted on a gram scale. A novel copper-mediated formylation using the widely available DMF as the formylation reagent and environmentally friendly molecular oxygen as the oxidant has also been developed. This protocol also provided a convenient approach for the synthesis of clinically used saripidem.

Copper- and DMF-mediated switchable oxidative C-H cyanation and formylation of imidazo[1,2-a]pyridines using ammonium iodide.

[4+1] cyclization of benzohydrazide and ClCF2COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5

Electrochemical routes for the synthesis of N-sulfonyl amidines and 1,3,4-oxadiazoles are reported through the activation of DMF molecule. Successful implementation of electro-redox on dehydrative coupling and oxidative cyclization reactions eliminates the necessity of stoichiometric chemical oxidants and minimizes the generation of reagent waste. Both protocols exhibited broad functional group tolerance, permitting a widespread substrate scope with 47–94% isolated yield. Several control experiments and cyclic voltammetry studies were performed and mechanistic details of these transformations are thoroughly outlined. 

Synthesis of N‐Sulfonyl Amidines and 1,3,4‐Oxadiazoles through Electrochemical Activation of DMF

Tandem synthesis, antibacterial evaluation and SwissADME prediction study of new bis(1,3,4-oxadiazoles) linked to arene units

DMF as Methine Source: Copper‐Catalyzed Direct Annulation of Hydrazides to 1,3,4‐Oxadiazoles

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DMF as Methine Source: Copper‐Catalyzed Direct Annulation of Hydrazides to 1,3,4‐Oxadiazoles