- Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives
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An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.
- Zuo, Youpeng,He, Xinwei,Tang, Qiang,Hu, Wangcheng,Zhou, Tongtong,Shang, Yongjia
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supporting information
p. 3890 - 3894
(2020/05/18)
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- 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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p. 3612 - 3618
(2019/07/10)
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- A Silver-Catalyzed Modular Intermolecular Access to 6,6-Spiroketals
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A modular synthesis of 6,6-spiroketals via silver catalysis is reported. By combining an intermolecular Michael addition and a 6-endo-dig cyclization, this cascade reaction allows the modular preparation of highly substituted 6,6-spiroketals by combining two substrate molecules. Established methods accessing this interesting substructure are complemented by this new transformation. The protocol tolerates diverse substitution patterns and functional groups. (Figure presented.).
- Ahrens, Alexander,Heinrich, Niklas F.,Kohl, Simon R.,Hokamp, Martha,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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supporting information
p. 5605 - 5615
(2019/12/11)
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- Chemo- and Regioselective Catalyst-Controlled Carbocyclization of Alkynyl Ketones: Rapid Synthesis of 1-Indanones and 1-Naphthols
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A catalyst-controlled intramolecular carbocyclization of 2-alkynyl aryl ketones is presented. Under rhodium(III) catalysis, 1-indanones are formed through 5-exo-dig carbocyclizations with exclusive chemo-, regio- and stereoselectivity. When catalyzed by copper(I), 1-naphthols are obtained through 6-endo-dig carbocyclizations with exclusive chemo- and regioselectivity.
- Song, Liangliang,Tian, Guilong,Van der Eycken, Erik V.
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supporting information
p. 7645 - 7648
(2019/05/21)
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- Radical-Triggered Tandem Cyclization of 1,6-Enynes with H2O: A Way to Access Strained 1 H-Cyclopropa[ b]naph thalene-2,7-diones
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A radical-triggered tandem cyclization of 1,6-enynes has been developed herein. Strained 1H-cyclopropa[b]naphthalene-2,7-diones are successfully obtained in moderate to good yields with excellent stereoselectivity. Mechanistic studies reveal a key role of water in generating a hydroxyl radical that initiates a sequential Michael addition/ring closure pathway. Importantly, the formed hydroxyl is proposed to be a good leaving group during the cyclopropane ring formation.
- Zheng, Limeng,Zhou, Bingwei,Jin, Hongwei,Li, Ting,Liu, Yunkui
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supporting information
p. 7053 - 7056
(2018/11/24)
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- Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway
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Dig this: 5-exo-dig carbocyclization of 1 into 2 features intramolecular carbopalladation of alkyne with Pd enolate (see scheme). DFT calculations show that the key Pd enolate forms by deprotonation assisted byb PdII acetate. Subsequent intramo
- Chernyak, Natalia,Gorelsky, Serge I.,Gevorgyan, Vladimir
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supporting information; experimental part
p. 2342 - 2345
(2011/04/18)
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