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Pulsed electrolysis enables unexpected lactonization of bicyclobutane carboxylic acids
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DOI：10.1039/D6SC01541G.png)
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Abstract
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Anodic oxidation of bicyclobutane carboxylic acids leads to unexpected lactonization and provides access to substituted benzene bioisosteres from highly strained precursors. High selectivity was achieved under pulsed electrolysis. Mechanistic experiments; supported by computational analysis; indicate that the transformation is initiated by single-electron oxidation of the substrate to form a bicyclobutyl radical cation; a key intermediate in redox-mediated transformations. These results demonstrate the utility of electrochemical methods for controlling the reactivity of bicyclobutane derivatives and provide a foundation for further development of sustainable oxidative transformations of strained molecules.
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