Formal allylic C(sp3)-H alkylation of α-alkylstyrenes by rearrangement of intermediate alkenyl sulfonium salts

Metal-free allylic C(sp(3))-H alkylation of alpha-alkylstyryl sulfonium salts based on [2,3]-sigmatropic rearrangement strategies has been developed. This operationally simple protocol enables allylic C(sp(3))-H alkylation of a wide range of alpha-alkylstyryl sulfonium salts. Notably, this method could allow facile access to allylated carbon quaternary centers in moderate to good yields. The one-pot procedure, product derivatization and late-stage functionalization all show the potential practicality of this protocol in organic synthesis.

Automated summary

A metal-free allylic C(sp(3))-H alkylation method based on [2,3]-sigmatropic rearrangement strategies has been developed, allowing the allylic C(sp(3))-H alkylation of a wide range of alpha-alkylstyryl sulfonium salts. This protocol enables facile access to allylated carbon quaternary centers in moderate to good yields. The one-pot procedure, product derivatization, and late-stage functionalization demonstrate the practicality of this protocol in organic synthesis.