Electrochemical selenium-π-acid promoted hydration of alkynyl phosphonates

An unprecedented electrochemical selenium-pi-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.

Automated summary

An unprecedented electrochemical selenium-pi-acid promoted hydration of internal alkynes bearing a phosphonate auxiliary is described. The reaction provides a mild and metal-free method for the synthesis of valuable ketones, demonstrating high atom-economy, good selectivity, and excellent functional group tolerance. Phosphonate assistance is proven to be essential for this transformation.