Efficient nucleophilic aromatic substitution between aryl nitrofluorides and alkynes.
The nucleophilic aromatic substitution reaction between electron-deficient aryl fluorides and terminal alkynes is shown to be efficiently promoted by sodium bis(trimethylsilyl)amide as a base. Moderate to excellent yields of 2-ethynylnitrobenzene products can be obtained under mild conditions.
DeRoy
Patrick L
PL
Department of Chemistry, Boehringer Ingelheim (Canada) Ltd, Research and Development, 2100 Cunard Street, Laval, Quebec, Canada.
Surprenant
Simon
S
Bertrand-Laperle
Megan
M
Yoakim
Christiane
C
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D005459:Fluorides / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D008670:Metals; D008968:Molecular Conformation; D012997:Solvents; D013237:Stereoisomerism
D000480:Alkynes; D006841:Hydrocarbons, Aromatic; D008670:Metals; D012997:Solvents; D005459:Fluorides