Metal-free aryltrifluoromethylation of activated alkenes.

@article{Kong2013MetalfreeAO,
  title={Metal-free aryltrifluoromethylation of activated alkenes.},
  author={Wangqing Kong and Mar{\'i}a Casimiro and Noelia Fuentes and Est{\'i}baliz Merino and Cristina Nevado},
  journal={Angewandte Chemie},
  year={2013},
  volume={52 49},
  pages={
          13086-90
        }
}
Metal-free: The first metal-free aryltrifluoromethylation of activated alkenes has been developed. With this method, trifluoromethylated isoquinolinediones, spirobicycles, oxindoles, and α-aryl-β-trifluoromethylamides were obtained with high control of the regioselectivity. 
213 Citations
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
Metal‐Free Aryltrifluoromethylation of Activated Alkenes.
Bu4NI is able to activate Togni reagent (II) to generate a highly reactive iodine (III) species, which smoothly reacts with alkenes to form a new C—CF3 bond.
One pot and selective intermolecular aryl- and heteroaryl-trifluoromethylation of alkenes by photoredox catalysis.
TLDR
Under the optimized conditions using Umemoto's reagent as a CF3 source, a wide range of styrenes can be readily difunctionalized, affording the corresponding trifluoromethylated adducts in up to 99% yield.
Transition metal free decarboxylative fluoroalkylation of N-acrylamides with 3,3,3-trifluoro-2,2-dimethylpropanoic acid (TFDMPA).
A novel transition metal-free decarboxylative fluoroalkylation of activated alkenes and C-H functionalization cascade process has been developed. This approach provides an efficient way to construct
Silver-mediated radical aryltrifluoromethylthiolaton of activated alkenes.
TLDR
The first example of silver-mediated oxidative aryltrifluoromethylthiolation of activated alkenes to produce valuable trifluors containing oxindoles was developed, providing a practical and easy-handling method to generate a F3CS(•) radical in the laboratory.
Iron-catalyzed radical aryldifluoromethylation of activated alkenes to difluoromethylated oxindoles.
An iron-catalyzed aryldifluoromethylation of activated alkenes under mild reaction conditions has been developed, which is a rare example where a cosolvent is used to improve the reaction yield along
Copper-Catalyzed Aminoarylation of Alkenes via Aminyl Radical Addition and Aryl Migration.
We describe a new strategy for aminoarylation of alkenes by copper-catalyzed smiles rearrangement using O-benzoylhydroxylamines as the amine reagent. This method affords various β-amino amide
A metal-free yne-addition/1,4-aryl migration/decarboxylation cascade reaction of alkynoates with Csp(3)-H centers.
A metal-free cascade reaction of aryl alkynoates with five different types of radical precursors (R-H) through an yne-addition/1,4-aryl migration/decarboxylation process was reported, which allowed
Metal-free direct trifluoromethylation of activated alkenes with Langlois' reagent leading to CF3-containing oxindoles.
TLDR
The present methodology, which utilizes very cheap CF3 reagent and a simple oxidant, provides a convenient and practical approach to CF3-containing oxindoles with a wide variety of functional groups.
...
...

References

SHOWING 1-10 OF 48 REFERENCES
Metal-free oxidative hydroxyalkylarylation of activated alkenes by direct sp3 C-H functionalization of alcohols.
A metal-free tandem radical addition/cyclization reaction of activated alkenes and alcohols has been developed. The process provides an efficient and atom economical access to various valuable
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
Recent developments on the trifluoromethylation of (hetero)arenes.
TLDR
This Focus review gives an overview over the recent development of trifluoromethylation of (hetero)arenes in Aryl-CF(3).
Aromatic trifluoromethylation catalytic in copper.
TLDR
Cu(I)-diamine complexes were found to catalyse the trifluoromethylation of aryl iodides and the cross-coupling reactions of iodoarenes with trif fluorine-based aromatics proceeded smoothly to afford triffluorometHylsilanes in good yields.
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 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 oxytrifluoromethylation of unactivated alkenes.
A mild, versatile, and convenient method for the efficient oxytrifluoromethylation of unactivated alkenes based on a copper-catalyzed oxidative difunctionalization strategy has been developed. This
Iodine(III)-mediated tandem acetoxylation-cyclization of o-acyl phenols for the facile construction of alpha-acetoxy benzofuranones.
An efficient tandem acetoxylation-cyclization of o-acylphenols mediated by the combination of iodobenzene diacetate with tetrabutylammonium iodide provides a new convenient and useful route to
Palladium-catalyzed carbo-heterofunctionalization of alkenes for the synthesis of oxindoles and spirooxindoles.
A palladium-catalyzed oxidative carbo-heterofunctionalization of aniline derivatives involving concomitant direct C-H functionalization and C-X bond formation was developed. By simply changing the
...
...