172607-53-3Relevant articles and documents
A Mild and Regioselective Synthesis of α-Fluoroketones via Gold and Selectfluor Partnership
Chen, Xi,Martini, Sophie,Michelet, Véronique
supporting information, p. 3612 - 3618 (2019/07/10)
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.).
Copper-catalyzed cascade cyclization of 1,5-enynes: Via consecutive trifluoromethylazidation/diazidation and click reaction: Self-assembly of triazole fused isoindolines
Yu, Liu-Zhu,Wei, Yin,Shi, Min
, p. 13163 - 13166 (2016/11/09)
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.
An indenone synthesis involving a new aminotransfer reaction and its application to dibenzopentalene synthesis
Katsumoto, Kenta,Kitamura, Chitoshi,Kawase, Takeshi
experimental part, p. 4885 - 4891 (2011/10/31)
o-(Phenylethynyl)phenyllithiums, generated by treatment of o-(phenylethynyl)bromobenzenes with tBuLi, were quenched with N,N-dimethylcarboamides to afford various 2-phenylindenone derivatives in moderate to good yields upon acidic workup. The choice of lithiation reagents was critical. When n-butyllithium was used the yields were reduced. The N-alkyl groups in the carboamides were also important: quenching with N,N-diethylbenzamides also afforded 2,3-diphenylindenones as the sole isolated products, but quenching with N-benzoylpiperidine led to 2-benzoyltolane in good yield. Control experiments revealed that the reactions proceed through a multi-step reaction sequence involving a novel intramolecular transamination to the α-acetylenic carbon of the alkynyl group. The method was applicable to the synthesis of dibenzopentalene derivatives as well as various indenone derivatives. A mechanism for the reaction is discussed.
