Copper-catalyzed intramolecular trifluoromethylation of N-benzylacrylamides coupled with dearomatization: access to CF3-containing 2-azaspiro[4.5]decanes.

@article{Han2014CoppercatalyzedIT,
  title={Copper-catalyzed intramolecular trifluoromethylation of N-benzylacrylamides coupled with dearomatization: access to CF3-containing 2-azaspiro[4.5]decanes.},
  author={Guifang Han and Yuxiu Liu and Qingmin Wang},
  journal={Organic letters},
  year={2014},
  volume={16 12},
  pages={
          3188-91
        }
}
Copper-catalyzed intramolecular trifluoromethylation of N-benzylacrylamides coupled with dearomatization was achieved and used to regiospecifically construct a variety of trifluoromethylated 2-azaspiro[4.5]decanes bearing adjacent quaternary stereocenters under mild conditions in moderate to excellent yields. 
57 Citations
Copper‐Catalyzed Intramolecular Trifluoromethylation of N‐Benzylacrylamides Coupled with Dearomatization: Access to CF3‐Containing 2‐Azaspiro[4.5]decanes.
Transformation of the methacrylamide analogue of the acrylamide (Ia) fails to give the corresponding 3-azaspiro[5.5]undecane derivative.
Copper-Catalyzed Phosphonylation/Trifluoromethylation of N-p-NO2-Benzoylacrylamides Coupled with Dearomatization and Denitration.
A novel and efficient copper-tert-butyl hydroperoxide mediated intramolecular spirocyclization of N-p-NO2-benzoylacrylamides through a cascade radical
Silver-catalyzed carbon-phosphorus functionalization of N-(p-methoxyaryl)propiolamides coupled with dearomatization: access to phosphorylated aza-decenones.
Silver-catalyzed cascade difunctionalization of N-(p-methoxyaryl)propiolamides coupled with dearomatization was achieved and used to regiospecifically construct a variety of phosphorylated
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.
Copper‐Catalyzed Trifluoromethylation of Acrylamides Coupled with Indole Dearomatization: Access to Trifluoromethyl‐Substituted Spiro[indole‐3,3′‐pyrrolidine] Derivatives
A copper-catalyzed cascade reaction involving trifluoromethylation of acrylamides coupled with ring closure and indole dearomatization is reported. This facile transformation was highly
Copper-catalyzed trifluoromethylation of alkenes: synthesis of trifluoromethylated benzoxazines.
A simple base and ligand free copper catalyzed method for the construction of trifluoromethylated benzoxazines has been developed by using Umemoto's reagent. It involves the oxidative
Visible light-induced intramolecular dearomative cyclization of α-bromo-N-benzyl-alkylamides: efficient construction of 2-azaspiro[4.5]decanes.
An efficient intramolecular dearomative cyclization via visible light-induced photoredox catalysis allows for a highly regioselective dearomative cyclization of α-bromo-N-benzyl-alkylamides to
Palladium-catalyzed difunctionalization/dearomatization of N-benzylacrylamides with α-carbonyl alkyl bromides: facile access to azaspirocyclohexadienones.
TLDR
An efficient palladium-catalyzed difunctionalization/dearomatization of N-benzylacrylamides with α-carbonyl alkyl bromides with β-bromoalkyl esters and ketones reacted smoothly to provide important azaspirocyclohexadienones in moderate to excellent yields.
Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction: approach to thiazole-fused pyrrolidinones with a C2-azaquarternary center.
A Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction for the construction of thiazole-fused pyrrolidinones with a C2-azaquarternary center and C3-exo-double bond has been achieved
Iron-catalyzed cascade cyanoalkylation/radical dearomatization of N-phenylcinnamamides: access to cyanoalkylated 1-azaspiro[4.5]decanes
An iron-catalyzed cascade radical cyanoalkylative dearomatization of N-phenyl cinnamamides was developed. A direct access to the 1-azaspiro[4.5]decanes motif with good regioselectivity and
...
...

References

SHOWING 1-10 OF 52 REFERENCES
Copper-catalyzed one-pot trifluoromethylation/aryl migration/desulfonylation and C(sp2)-N bond formation of conjugated tosyl amides.
A novel copper-catalyzed one-pot trifluoromethylation/aryl migration/desulfonylation and C(sp(2))-N bond formation with conjugated tosyl amides as starting materials is presented here. The reaction
Copper-catalyzed intermolecular trifluoromethylazidation of alkenes: convenient access to CF3 -containing alkyl azides.
TLDR
A novel copper-catalyzed intermolecular trifluoromethylazidation of alkenes has been developed under mild reaction conditions and can be easily transformed into the corresponding CF3 -containing amine derivatives.
Copper-catalyzed synthesis of trifluoromethyl-substituted isoxazolines.
A mild and efficient copper-catalyzed trifluoromethylation reaction which involves the cyclization of oximes has been developed. This method provides a convenient access to a variety of useful
Iron-catalyzed trifluoromethylation with concomitant C-C bond formation via 1,2-migration of an aryl group.
Iron-catalyzed trifluoromethylation with concomitant 1,2-migration of an aryl group starting from diaryl allyl alcohol was achieved under mild conditions. This reaction system affords
Trifluoromethylation reactions for the synthesis of β-trifluoromethylamines.
A multitalented system: N-migratory oxytrifluoromethylation and one-pot three-component reactions of allylamines as well as the aminotrifluoromethylation of alkenyl amines all proceeded efficiently
Copper-catalyzed trifluoromethylation of terminal alkenes through allylic C-H bond activation.
TLDR
Both experimental and theoretical analyses indicate that the trifluoromethylation may occur via a Heck-like four-membered-ring transition state.
Electrophilic trifluoromethylation by copper-catalyzed addition of CF3-transfer reagents to alkenes and alkynes.
TLDR
Regio- and stereoselective Cu-catalyzed addition of the above hypervalent iodine reagent to alkynes and alkenes was achieved, andAlkenes react faster than alkynes emphasizing the electrophilic character of the addition reaction.
Copper-catalyzed oxidative trifluoromethylation of terminal alkenes using nucleophilic CF3SiMe3: efficient C(sp3)-CF3 bond formation.
An efficient C(sp(3))-CF(3) bond-forming reaction via Cu-catalyzed oxidative trifluoromethylation of terminal alkenes has been developed, which proceeds under mild conditions using readily available,
Metal-free direct intramolecular carbotrifluoromethylation of alkenes to functionalized trifluoromethyl azaheterocycles.
The first example of a metal-free direct carbotrifluoromethylation of alkenes using inexpensive TMSCF3 as the CF3 source is described. The methodology not only exhibits high chemoselectivity for this
Copper(I)-catalyzed diastereoselective hydroxytrifluoromethylation of dienes accelerated by phosphine ligands
A diastereoselective 1,4-hydroxytrifluoromethylation of dienes is catalyzed by copper cyanide–phosphine complexes. This reaction is significantly accelerated by bulky monodentate phosphines, and the
...
...