- A Mild and Regioselective Synthesis of α-Fluoroketones via Gold and Selectfluor Partnership
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An efficient, mild and rapid synthesis of α-fluoroketones has been developed, via a fruitful association between gold and Selectfluor starting from aldehyde-yne and alkynylaryl ketone derivatives. Several functionalized and synthetically highly valuable α-fluoroketones (21 compounds, up to 92%) were isolated in good to excellent yields via a remarkable regioselective oxyfluorination reaction in EtOH/H2O at room temperature. We have shed some light on parts of the mechanism by reacting diphenylacetylene and aldehyde-yne with or without Selectfluor. The reaction most presumably occurs via a sequential gold-catalyzed regioselective hydration followed by the α-fluorination reaction, but the presence of aldehyde moiety is crucial for the reactivity of alkyne function. The fluoroketones were efficiently transformed to 4-fluoroisoquinolines (9 compounds, 82–95%) of high pharmaceutical interest. (Figure presented.).
- Chen, Xi,Martini, Sophie,Michelet, Véronique
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supporting information
p. 3612 - 3618
(2019/07/10)
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- Gold-catalyzed Intermolecular Oxidations of 2-Ketonyl-1-ethynyl Benzenes with N-Hydoxyanilines to Yield 2-Aminoindenones via Gold Carbene Intermediates
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Gold-catalyzed oxidations of 2-ketonyl-1-ethynyl benzenes with N-hydroxyanilines yield 2-aminoindenone derivatives efficiently. Experimental data suggests that this process involves an α-oxo gold carbene intermediate, generated from the attack of N-hydroxyaniline on furylgold carbene intermediate, rather than the typical attack of oxidants on π-alkynes.
- Mokar, Bhanudas Dattatray,Huple, Deepak B.,Liu, Rai-Shung
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p. 11892 - 11896
(2016/11/16)
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- Copper-catalyzed cascade cyclization of 1,5-enynes: Via consecutive trifluoromethylazidation/diazidation and click reaction: Self-assembly of triazole fused isoindolines
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Copper-catalyzed cascade cyclization of 1,5-enynes with two types of hypervalent reagents was developed via consecutive trifluoromethylazidation/diazidation and intramolecular click reaction (CUAAC), providing one-pot self-assembly of triazole fused isoindolines bearing a trifluoromethyl or an azide moiety. Moreover, the construction of a trifluoromethylcyclopropyl unit, which has been considered as a metabolically stable replacement for a tert-butyl moiety and was difficult to access, was also achieved under trifluoromethylazidation conditions. All these reactions exhibited excellent chemoselectivity, good to excellent yields and broad functional group tolerance.
- Yu, Liu-Zhu,Wei, Yin,Shi, Min
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supporting information
p. 13163 - 13166
(2016/11/09)
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- Synthesis of isoindole derivatives by palladium-catalyzed domino reaction of (2-alkynyl)phenylketone o-pentafluorobenzoyloximes
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Isoindole derivatives were synthesized by the palladium-catalyzed cyclization of (2-alkynyl)phenylketone O-pentafluoro-benzoyloximes in the presence of organometallic compounds such as sodium formate and aryl boronic acid. Georg Thieme Verlag Stuttgart - New York.
- Kitamura, Mitsuru,Moriyasu, Yohei,Okauchi, Tatsuo
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p. 643 - 646
(2011/05/02)
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- SUBSTITUTED PHENYLETHYNYL GOLD-NITROGENATED HETEROCYCLIC CARBENE COMPLEX
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The present invention is directed to a substituted phenylethynylgold-nitrogen-containing heterocyclic carbene complex represented by the formula (1) or (2): wherein L represents a nitrogen-containing heterocyclic carbene ligand, and X represents an alkyl
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