Synthesis of Acyclic Quaternary α-CF-β-Oxo Carbonyls via Nucleophilic Substitution Induced by Single-Electron Transfer

The development of efficient methods for the formation of quaternary centers in organic compounds has been a constant challenge in synthetic chemistry. Quaternary β-oxo esters are fundamental structures in the synthesis of natural products, pharmaceutical compounds, and other bioactive molecules. In this work, a direct and versatile approach to quaternary noncyclic β-oxo esters is reported using trifluoromethyl thianthrenium salt as highly reactive and selective reagent under mild conditions. Mechanistic investigations supported the operation via single-electron transfer-induced nucleophilic substitution.