TY - JOUR
T1 - PdH-Electrocatalytic Formal Conjugate Fluorination of β-Aryl-α,β-Unsaturated Amides with Mild and Safe Nucleophilic Fluorine Sources
AU - Yang, Baeho
AU - Lee, Dohyun
AU - Shin, Kwangmin
N1 - Publisher Copyright:
© 2025 American Chemical Society.
PY - 2025
Y1 - 2025
N2 - An electrooxidative palladium-hydride catalytic system has been developed for the hydrofluorination of β-aryl-α,β-unsaturated amides using various nucleophilic fluorine sources, including Me4NF, Me4NF·tAmylOH, nBu4NF·(tBuOH)4, CsF, and KF. By avoiding hazardous HF-based reagents, this electrocatalytic protocol offers a safer and more practical route for the formal conjugate addition of fluoride to β-aryl-α,β-unsaturated amides, enabling access to β-fluoroamides. The method exhibits broad functional group tolerance, as exemplified by its application to the late-stage derivatization of complex molecules.
AB - An electrooxidative palladium-hydride catalytic system has been developed for the hydrofluorination of β-aryl-α,β-unsaturated amides using various nucleophilic fluorine sources, including Me4NF, Me4NF·tAmylOH, nBu4NF·(tBuOH)4, CsF, and KF. By avoiding hazardous HF-based reagents, this electrocatalytic protocol offers a safer and more practical route for the formal conjugate addition of fluoride to β-aryl-α,β-unsaturated amides, enabling access to β-fluoroamides. The method exhibits broad functional group tolerance, as exemplified by its application to the late-stage derivatization of complex molecules.
UR - https://www.scopus.com/pages/publications/105010125661
U2 - 10.1021/acs.joc.5c01032
DO - 10.1021/acs.joc.5c01032
M3 - Article
AN - SCOPUS:105010125661
SN - 0022-3263
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
ER -