Copper‐Catalyzed Trifluoromethylation of Acrylamides Coupled with Indole Dearomatization: Access to Trifluoromethyl‐Substituted Spiro[indole‐3,3′‐pyrrolidine] Derivatives

@article{Han2016CopperCatalyzedTO,
  title={Copper‐Catalyzed Trifluoromethylation of Acrylamides Coupled with Indole Dearomatization: Access to Trifluoromethyl‐Substituted Spiro[indole‐3,3′‐pyrrolidine] Derivatives},
  author={Guifang Han and Qiang Wang and Linwei Chen and Yu‐Xin Liu and Qingmin Wang},
  journal={Advanced Synthesis \& Catalysis},
  year={2016},
  volume={358},
  pages={561-566}
}
A copper-catalyzed cascade reaction involving trifluoromethylation of acrylamides coupled with ring closure and indole dearomatization is reported. This facile transformation was highly regioselective and proceeded under mild conditions, allowing efficient access to trifluoromethyl-substituted spiro[indole-3,3′-pyrrolidine] derivatives, which are of increasing interest to the pharmaceutical industry. 
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25 Citations

25 Citations

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Citation Type

Copper-Catalyzed Trifluoromethylation of Ynones Coupled with Dearomatizing Spirocyclization of Indoles: Access to CF3-Containing Spiro[cyclopentane-1,3'-indole].
TLDR
This cascade process enables constructing diverse CF3-containing spiro[cyclopentane-1,3'-indole] scaffolds in moderate to excellent yields which have challenging quaternary spirocyclic carbon and tetrasubstituted alkenes.
Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides.
TLDR
An efficient method for the synthesis of difluoroalkylated 2-azaspiro and saturated spirocyclohexanone scaffold via copper-catalyzed difleudoalkylation of N-benzylacrylamides with ethyl bromodifluorosoroacetate has been established.
Palladium-Catalyzed Tandem Carbocyclization and Hetroarylation for the Synthesis of 2-(Trifluoromethyl)indenylmethyleneindoles.
TLDR
A palladium-catalyzed tandem cyclization and cross-coupling reaction of o-(2-chlorovinyl)alkynylbenzenes with indoles/pyrroles is developed to afford previously unknown trifluoromethyl-containing indenylmethyleneindoles, which are potentially useful in drug design.
Direct Synthesis of Sulfonylated Spiro[indole-3,3'-pyrrolidines] by Silver-Mediated Sulfonylation of Acrylamides Coupled with Indole Dearomatization.
A dearomative tandem spiro-cyclization reaction of N-[(1H-indol-3-yl)methyl]methacrylamide derivatives with sulfinate sodium in the presence of AgNO3 and K2CO3 is reported, which produced…
Copper-catalyzed radical cascade cyclization for synthesis of CF3-containing tetracyclic benzimidazo[2,1-a]iso-quinolin-6(5H)-ones.
Here, a general copper-catalyzed radical cascade carbocyclization reaction with 2-arylbenzoimidazoles and a Togni reagent was realized. Structurally diverse CF3-containing tetracyclic core…
Aryltrifluoromethylative cyclization of unactivated alkenes by the use of PhICF3Cl under catalyst-free conditions.
TLDR
A concise and catalyst-free aryltrifluoromethylative cyclization of unactivated alkenes has been developed and would make this method well-suited for applications.
Synthesis of trifluoroalkyl or difluoroalkyl phenanthridine derivatives via cascade reaction using an intramolecular cyano group as a radical acceptor under photoredox catalysis.
In the presence of Ru(phen)3Cl2 or fac-Ir(ppy)3 under visible-light irradiation, the addition of fluorinated radicals to N-arylacrylamides followed by an intramolecular cyano group insertion cascade…
Control of site selectivity in trifluoromethylation of alkenes bearing a pendant indolyl group: Synthesis of CF3-containing tetrahydrocarbazoles
Synthesis of C3-Methyl-Substituted Pyrroloindolines and Furoindolines via Cascade Dearomatization of Indole Derivatives with Methyl Iodide.
TLDR
A highly efficient method for constructing C3-methyl-substituted pyrroloindoline and furoindolines via cascade dearomatization reaction of indole derivatives with methyl iodide was developed and demonstrated in the concise synthesis of (±)-esermethol.
Catalyst-free and selective trifluoromethylative cyclization of acryloanilides using PhICF3Cl.
TLDR
This work describes a catalyst-free protocol to innately produce electrophilic CF3 species from PhICF3Cl for trifluoromethylative cyclization of acryloanilides.
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