Hypervalent iodine catalysis enabled iterative multi-fluorination: not just a simple alternative for the electrochemical approach.

Unlike the well-established fluoroalkylation, the direct incorporation of multiple fluorine atoms into small molecules iterative fluorinations has been much less investigated. Herein, we report a hypervalent iodine catalytically selective multi-fluorination in which the fluorination degree is controlled by the delicate balance between the HF/amine ratios. The and of hypervalent iodine catalysis and the previously established electrochemical approach in the iterative multi-fluorinations are also provided.

Current-Controlled Electrochemical Approach Toward Mono- and Trifluorinated Isoindolin-1-one Derivatives.

An electrochemical intramolecular 5- aza-cyclization of 2-alkynylbenzamides and subsequent nucleophilic fluorination have been developed to afford the highly selective synthesis of mono- and trifluorinated isoindolin-1-one derivatives. This work demonstrates the unique capability of synthetic electrochemistry in controlling reaction selectivity through the applied electrolytic parameters. In addition, the obtained monofluorinated 3-methyleneisoindolin-1-one () displays interesting photophysical properties that are not observed in its nonfluorinated analog.

Desulfonylative Electrocarboxylation with Carbon Dioxide.

Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.