Addition of CF3 across unsaturated moieties: a powerful functionalization tool

@article{Merino2014AdditionOC,
  title={Addition of CF3 across unsaturated moieties: a powerful functionalization tool},
  author={Est{\'i}baliz Merino and Cristina Nevado},
  journal={Chemical Society Reviews},
  year={2014},
  volume={43},
  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. 
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471 Citations
Background Citations
2
Methods Citations
2

471 Citations

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NHC-Catalyzed Electrophilic Trifluoromethylation: Efficient Synthesis of γ-Trifluoromethyl α,β-Unsaturated Esters.
TLDR
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.
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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.
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.
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.
Nucleophilic fluoroalkylation of terminal vinyl triflones with SO2CF3 as a removable activating group
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