Organic Chemistry Portal



Photochemical C-F Activation Enables Defluorinative Alkylation of Trifluoroacetates and -Acetamides

Mark W. Campbell, Viktor C. Polites, Shivani Patel, Juliette E. Lipson, Jadab Majhi and Gary A. Molander*

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States, Email:

M. W. Campbell, V. C. Polites, S. Patel, J. E. Lipson, J. Majhi, G. A. Molander, J. Am. Chem. Soc., 2021, 143, 19648-19654.

DOI: 10.1021/jacs.1c11059

see article for more reactions


A photochemically mediated defluorinative hydroalkylation of ethyl trifluoroacetate with a diverse suite of alkenes in the presence of sodium formate enables a concise synthetic approach to novel gem-difluoro analogs of FDA-approved pharmaceutical compounds. Furthermore, trifluoroacetamides can also be functionalized via synergistic Lewis acid/photochemical activation.

see article for more examples

Key Words

α-fluorocarboxylic esters, alkylation, sodium formate, photochemistry

ID: J48-Y2021