Addition of CF3 across unsaturated moieties: a powerful functionalization tool

  title={Addition of CF3 across unsaturated moieties: a powerful functionalization tool},
  author={Est{\'i}baliz Merino and Cristina Nevado},
  journal={Chemical Society Reviews},
  pages={6598 - 6608}
This review summarizes recent methodologies for the simultaneous formation of C–CF3 and C–C or C–heteroatom bonds by formal addition reactions to alkenes. 
Selective single C–F bond arylation of trifluoromethylalkene derivatives
Through an SN2′ amination, N-alkylation and palladium-catalyzed allylic substitution sequence, we realized ipso-C–F bond arylation/alkenylation of trifluoromethylalkene derivatives.
NHC-Catalyzed Electrophilic Trifluoromethylation: Efficient Synthesis of γ-Trifluoromethyl α,β-Unsaturated Esters.
Control experiments and DFT calculations provided important insight into the reaction mechanism and revealed a highly regioselective and efficient N-heterocyclic-carbene-catalyzed γ-trifluoromethylation of vinylogous enolates.
Copper-catalyzed regio- and stereoselective fluorocarboalkynylation of alkynes
It is attractive to establish an efficient and practical platform affording functional compounds using readily available feedstocks as starting materials under mild conditions.
Perfluoroalkylative pyridylation of alkenes via 4-cyanopyridine-boryl radicals
A metal- and photo-free method for the perfluoroalkylative pyridylation of alkenes has been developed.
CF3-Substituted semisquarate: a pluripotent building block for the divergent synthesis of trifluoromethylated functional molecules.
The first synthesis of a CF3-substituted semisquarate was accomplished via nucleophilic trifluoromethylation using CF3SiMe3 and subsequent rhenium-catalyzed allylic alcohol rearrangement. The
Rh(i)-Catalyzed regioselective arylcarboxylation of acrylamides with arylboronic acids and CO2
The first Rh(i)-catalyzed regioselective arylcarboxylation of electron-deficient acrylamides with arylboronic acids under atmospheric pressure of CO2 has been developed.
One pot and selective intermolecular aryl- and heteroaryl-trifluoromethylation of alkenes by photoredox catalysis.
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.
1,3-Difunctionalization of alkenes: state-of-the-art and future challenges
The direct difunctionalization of alkenes has emerged as a sustainable and versatile strategy for the efficient construction of complex molecules from simple chemical feedstocks. Specifically, the
Transition metal-free synthesis of fluoroalkylated oxindoles via base-mediated fluoroalkylation of N-arylacrylamides with RFI
A novel method for synthesizing fluoroalkylated oxindoles by the cyclization of N-arylacrylamides with fluoroalkyl iodide initiated with K2CO3 is reported.


Silver-catalyzed hydrotrifluoromethylation of unactivated alkenes with CF3SiMe3.
A silver-catalyzed hydrotrifluoromethylation of unactivated alkenes is described, which is a complementary method to electrophilic allylic triflorometHylation in the presence or absence of metal catalysts.
Trifluoromethylation of allylsilanes under copper catalysis.
The trifluoromethylation reactions are performed with Togni reagent (II) to give branched allylic trifluoromethylated products.
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
Copper-catalyzed C(sp3)-C(sp3) bond formation using a hypervalent iodine reagent: an efficient allylic trifluoromethylation.
This reaction provides a general and straightforward way to synthesize allylic trifluoromethylated compounds under mild conditions.
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
Recent developments on the trifluoromethylation of (hetero)arenes.
This Focus review gives an overview over the recent development of trifluoromethylation of (hetero)arenes in Aryl-CF(3).
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 N-arylacrylamides "on water" at room temperature.
A copper-catalyzed intramolecular trifluoromethylation of arylacrylamides leads to oxindole derivatives, effected with stable and inexpensive Langlois' reagent (CF3SO2Na) via a radical process in water at room temperature.
Silver-mediated trifluoromethylation-iodination of arynes.
An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF3 and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes