54081-33-3Relevant articles and documents
Decarboxylative Cross-Coupling of Acyl Fluorides with Potassium Perfluorobenzoates
Fu, Liyan,Chen, Qiang,Nishihara, Yasushi
supporting information, p. 6388 - 6393 (2020/08/24)
We report the transition metal-free decarboxylative cross-coupling reactions of acyl fluorides with potassium perfluorobenzoates. Compared with traditional transition metal-catalyzed cross-couplings, this protocol presents an extremely environmentally ben
Dehydrogenation of perfluoroalkyl ketones by using a recyclable oxoammonium salt
Hamlin, Trevor A.,Kelly, Christopher B.,Leadbeater, Nicholas E.
supporting information, p. 3658 - 3661 (2013/07/19)
A novel dehydrogenation reaction of perfluoroalkyl ketones by the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO+BF4-, Bobbitt's salt, 1) is described. The reaction proceeds under mildly basic conditions and appears to be unique to perfluoroalkyl ketones. A proposed mechanism for this unusual transformation is given. The byproduct of the reaction, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy (1a), can easily be recovered and used to regenerate the oxoammonium salt. The dehydrogenation of perfluoroalkyl ketones by using an oxoammonium salt is reported. The reaction proceeds under mildly basic conditions and affords α,β-unsaturated products in fair to excellent yields. The reaction likely proceeds through a two-step sequence. The spent oxidant can easily be recovered and used to regenerate the oxoammonium salt. Copyright
Graphite oxide as an auto-tandem oxidation-hydration-aldol coupling catalyst
Jia, Hong-Peng,Dreyer, Daniel R.,Bielawski, Christopher W.
supporting information; experimental part, p. 528 - 532 (2011/04/24)
Graphite oxide (GO) was found to function as an auto-tandem oxidation-hydration-aldol coupling catalyst for the formation of chalcones in a single reaction vessel. Various alkynes or alcohols were hydrated or oxidized in situ to their corresponding methyl ketones or aldehydes, respectively, which underwent a subsequent Claisen-Schmidt condensation. Each of the aforementioned reactions proceeded in the absence of metals (confirmed by inductively coupled plasma mass spectrometry, ICP-MS) and afforded a range of chalcone products in good to excellent yields from commercially available starting materials.