Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes

Mizuta, Satoshi; S. R. Stenhagen, Ida; O’Duill, Miriam; Wolstenhulme, Jamie; K. Kirjavainen, Anna; J. Forsback, Sarita; Tredwell, Matthew; Sandford, Graham; R. Moore, Peter; Huiban, Mickael; K. Luthra, Sajinder; Passchier, Jan; Solin, Olof; Gouverneur, Véronique

Abstract

Treatment of readily available α,α-difluoro- and α-fluoroarylacetic acids with Selectfluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stage fluorination strategy. Translation to [18F]labeling is demonstrated using [18F]Selectfluor bis(triflate), a reagent affording [18F]tri- and [18F]difluoromethylarenes not within reach with [18F]F2.

Citation

Mizuta, S., S. R. Stenhagen, I., O’Duill, M., Wolstenhulme, J., K. Kirjavainen, A., J. Forsback, S., Tredwell, M., Sandford, G., R. Moore, P., Huiban, M., K. Luthra, S., Passchier, J., Solin, O., & Gouverneur, V. (2013). Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes. Organic Letters, 15(11), 2648-2651. https://doi.org/10.1021/ol4009377

• Journal Article Type: Letter
• Online Publication Date: May 20, 2013
• Publication Date: Jun 7, 2013
• Deposit Date: Jul 31, 2023
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 15
• Issue: 11
• Pages: 2648-2651
• DOI: https://doi.org/10.1021/ol4009377
• Keywords: Organic Chemistry; Physical and Theoretical Chemistry; Biochemistry
• Public URL: https://nottingham-repository.worktribe.com/output/23554258
• Publisher URL: https://pubs.acs.org/doi/10.1021/ol4009377