Site-Selective Alkenylation of Unactivated C(sp3)-H Bonds Mediated by Compact Sulfate Radical

A broad variety of unactivated acyclic and alicyclic substrates cleanly undergo site-selective alkenylation of unactivated C(sp(3))-H bonds with 1,2-bis(phenylsulfonyl)ethene in the presence of persulfate. This simple transformation furnishes (E)-2-alkylvinylphenylsulfones in up to 88 % yield. In contrast with the previously reported decatungstate protocol, the current method is applicable to alkenylation of sterically hindered C-H bonds. This important advantage significantly broadens the substrate scope, and is attributed to the compact size of the sulfate radical employed in the C-H activation and cleavage.

Automated summary

A novel method has been developed for site-selective alkenylation of a broad variety of substrates, including sterically hindered acyclic and alicyclic substrates. This method allows for the generation of (E)-2-alkylvinylphenylsulfones in high yield by utilizing persulfate and 1,2-bis(phenylsulfonyl)ethene. The compact size of the sulfate radical employed in C-H activation and cleavage allows for the alkenylation of sterically hindered C-H bonds, broadening the scope of substrates that can be efficiently transformed.