Copper-Catalyzed Aryltrifluoromethylation of N-Phenylcinnamamides: Access to Trifluoromethylated 3,4-Dihydroquinolin-2(1 H)-ones

  title={Copper-Catalyzed Aryltrifluoromethylation of N-Phenylcinnamamides: Access to Trifluoromethylated 3,4-Dihydroquinolin-2(1 H)-ones},
  author={Qiang Wang and Guifang Han and Yu‐Xin Liu and Qingmin Wang},
  journal={Advanced Synthesis \& Catalysis},
16 Citations
A benzene-bridged divanadium complex-early transition metal catalyst for alkene alkylarylation with PhI(O2CR)2via decarboxylation.
Mechanistic studies revealed a relay sequence of decarboxylative radical alkylation/radical arylation/oxidative re-aromatization that was amenable to a wide range of functionalities on alkenes and HIRs.
Rhenium-catalyzed alkylarylation of alkenes with PhI(O2CR)2via decarboxylation to access indolinones and dihydroquinolinones
Rhenium-catalyzed alkylarylation of alkenes with hypervalent iodine(III) reagents (HIRs) via decarboxylation to access various 3,3-disubstituted indolinones and trans-3,4-dihydroquinolinones is
Visible-Light-Mediated [2+2+1] Carbocyclization Reactions of 1,7-Enynes with Bromofluoroacetate to Form Fused Monofluorinated Cyclopenta[c]quinolin-4-ones.
A new protocol for photoinduced radical [2+2+1] carbocyclization reactions of 1,7-enynes with bromofluoroacetate provides an efficient and general route to a variety of fused monofluorinated cyclopenta[c]quinolin-4-one derivatives.
Fluoroalkylation Methods for Synthesizing Versatile Building Blocks
In this account, we provide an overview of synthetic methods for accessing fluoroalkylated compounds via electrophilic fluoroalkylation, especially of alkenes, focusing mainly on our own studies di...
Fe-Catalyzed decarbonylative cascade reaction of N-aryl cinnamamides with aliphatic aldehydes to construct 3,4-dihydroquinolin-2(1H)-ones.
A practical Fe-catalyzed decarbonylative cascade reaction of N-aryl cinnamamides with aliphatic aldehydes to provide C3 alkylated 3,4-dihydroquinolin-2(1H)-ones is developed. Aliphatic aldehydes were
K2S2O8-Mediated Selective Trifluoromethylacylation and Trifluoromethylarylation of Alkenes under Transition-Metal-Free Conditions: Synthetic Scope and Mechanistic Studies.
Control experiments and DFT calculations indicate that the CF3SO2Na/K2S2O8 system is capable of trifluoromethylating the substrate of alkenes without a transition metal catalyst and the oxidation of CF3 SO2Na to ·CF3 by K2S 2O8 is involved in the rate-determining step.
Visible-Light-Promoted Cascade Alkene Trifluoromethylation and Dearomatization of Indole Derivatives via Intermolecular Charge Transfer.
This work provides facile access to spiroindolenines bearing a trifluoromethyl group enabled by visible light and in good yields merely upon the illumination of two starting materials in 1,2-dichloroethane solution at room temperature.
Metal‐Free Radical‐Triggered Selenosulfonation of 1,7‐Enynes for the Rapid Synthesis of 3,4‐Dihydroquinolin‐2(1H)‐ones in Batch and Flow
This room-temperature protocol provides a highly efficient approach to diverse selenosulfones in moderate to excellent yields and with a broad scope of substrates, and should provide a potential synthesis method for the construction of diverse and meaningful 3,4-dihydroquinolin-2(1H)-ones derivatives in the fields of pharmaceutical and biological chemistry.


Facile Synthesis of 3-Substituted and 1,3-Disubstituted Quinolin-2(1H)-ones from 2-Nitrobenzaldehydes
2-Nitrobenzaldehydes were reduced with iron powder to 2-aminobenzaldehydes, which were reacted immediately with acyl chlorides to provide 2-carboxamidobenzaldehydes (1) with overall yields of 71-90
Development and Challenges in the Copper-Catalyzed Trifluoromethylation of Alkenes
The recent trifluoromethylation of unactivated alkenes and related compounds provides a new and straightforward method to mainly form Csp3–CF3 bonds. However, several mechanisms have been proposed
Direct Trifluoromethylation of the CH Bond
Trifluoromethylation meets CH activation: after transition metal-catalyzed trifluoromethylation became more and more popular, trifluoromethylation via CH activation is now emerging as the latest
Trifluormethylierung von Alkenen unter gleichzeitiger Einführung weiterer funktioneller Gruppen
Die Trifluormethylgruppe ist Bestandteil vieler synthetischer bioaktiver Verbindungen, und die Difunktionalisierung von CC-Bindung wurde als wirksame Strategie zum Aufbau von Verbindungen mit
CF3-substituierte aromatische und heterocyclische Bausteine
Fluor bleibt ein Geheimtipp in den Lebenswissenschaften, da sich mit diesem Element biologische Eigenschaften abstimmen lassen. Die Synthese fluorhaltiger Zielverbindungen ist jedoch nicht immer