Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations

Ethynylbenziodoxolones (EBXs) are commonly encountered reagents for the electrophilic alkynylation of nucleophiles. Herein, we report a one-pot, two-step process for EBX generation and their direct application in substrate functionalization. Our approach enables us to bypass the originally mandatory isolation and purification of the reagents, resulting in a more efficient synthesis. We could apply this process to seven different transformations involving both two- and one-electron nucleophiles to obtain a large variety of alkynylated products.

Automated summary

In this study, a simplified synthesis method for generating Ethynylbenziodoxolones (EBXs) in one pot and directly applying them to substrate functionalization was reported. By bypassing the mandatory isolation and purification steps, this approach led to a more efficient synthesis and successful application in various transformations to obtain a diverse range of alkynylated products.