Bond cleavage

Catalysis

Engineering

Geotechnical engineering

Triple bond

Cleavage (geology)

Transition metal

Annulation

Stereochemistry

Formal synthesis

Medicinal chemistry

Combinatorial chemistry

Organic chemistry

Mathematics

Reagent

Mathematical analysis

Fracture (geology)

Double bond

Chemistry

Carboxylation

Base (topology)

Organic Letters

A practical method for the synthesis of 2,2-difluorinated 2,3-dihydrofurans has been established via the [4 + 1] annulation of enaminones and BrCF2CO2Et with Na2CO3 promotion. This new protocol does not employ any transition metal reagent and enables the annulative difluoromethylation by the partial cleavage of the C═C double bond. In addition, the further treatment with hydrochloric acid in one pot leads to β-keto enoic acids (4-oxo-2-butenoic acids) via a formal enaminone C-N carboxylation.

Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF<sub>2</sub>CO<sub>2</sub>Et toward 2,2-Difluorinated 2,3-Dihydrofurans

Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF2CO2Et toward 2,2-Difluorinated 2,3-Dihydrofurans

Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF₂CO₂Et toward 2,2-Difluorinated 2,3-Dihydrofurans