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Electrochemical selenium-π-acid promoted hydration of alkynyl phosphonates.

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An unprecedented electrochemical selenium-π-acid promoted hydration of internal alkynes bearing a phosphonate auxiliary was described. Thus, valuable (hetero)aryl and alkyl ketones could be accessed under mild, metal- and external oxidant-free… Click to show full abstract

An unprecedented electrochemical selenium-π-acid promoted hydration of internal alkynes bearing a phosphonate auxiliary was described. Thus, valuable (hetero)aryl and alkyl ketones could be accessed under mild, metal- and external oxidant-free conditions. This protocol features high atom-economy, good chemo- and regio-selectivity, excellent functional group tolerance and easily transformable products. Control experiments demonstrate that phosphonate assistance is essential for this transformation.

Keywords: selenium acid; promoted hydration; electrochemical selenium; acid promoted

Journal Title: Chemical communications
Year Published: 2022

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