Over the past decade, the most significant, conceptual advances in the field of fluorination were enabled most prominently by organo- and transition-metal catalysis. The most challenging transformation remains the formation of the parent C-F bond, primarily as a consequence of the high hydration energy of fluoride, strong metal-fluorine bonds, and highly polarized bonds to fluorine. Most fluorination reactions still lack generality, predictability, and cost-efficiency. Despite all current limitations, modern fluorination methods have made fluorinated molecules more readily available than ever before and have begun to have an impact on research areas that do not require large amounts of material, such as drug discovery and positron emission tomography. This Review gives a brief summary of conventional fluorination reactions, including those reactions that introduce fluorinated functional groups, and focuses on modern developments in the field.

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Introduction of Fluorine and Fluorine-Containing Functional Groups

Trifluoromethyltrimethylsilane: nucleophilic trifluoromethylation and beyond.

Carbon trifluoromethylation reactions of hydrocarbon derivatives and heteroarenes.

Energetic salts offer many advantages over conventional energetic molecular compounds. The use of nitrogen containing anions and cations contributes to high heats of formations and high densities. Their low carbon and hydrogen content gives rise to a good oxygen balance. The decomposition of these compounds is predominantly through the generation of dinitrogen which makes them very promising candidates for highly energetic materials for industrial or military applications.

Energetic nitrogen-rich salts and ionic liquids.

Monofluorination of Organic Compounds: 10 Years of Innovation.

Progress in 1,2,3,4-tetrazine chemistry.

This study presents the first synthesis and characterization of a new high energy compound [1,2,3,4]tetrazino[5,6-e][1,2,3,4]tetrazine 1,3,6,8-tetraoxide (TTTO). It was synthesized in ten steps from 2,2-bis(tert-butyl-NNO-azoxy)acetonitrile. The synthetic strategy was based on the sequential closure of two 1,2,3,4-tetrazine 1,3-dioxide rings by the generation of oxodiazonium ions and their intramolecular coupling with tert-butyl-NNO-azoxy groups. The TTTO structure was confirmed by single-crystal X-ray.

Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO).

Chiral Ionic Liquids Bearing O-Silylated α,α-Diphenyl (S)- or (R)-Prolinol Units: Recoverable Organocatalysts for Asymmetric Michael Addition of Nitroalkanes to α,β-Enals

Vladimir A. Tartakovsky

Papers

Progress in 1,2,3,4-tetrazine chemistry.

Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO).

Chiral Ionic Liquids Bearing O-Silylated α,α-Diphenyl (S)- or (R)-Prolinol Units: Recoverable Organocatalysts for Asymmetric Michael Addition of Nitroalkanes to α,β-Enals

Nucleophilic Trifluoromethylation of Imines under Acidic Conditions

Synthesis of [1,2,5]Oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-Di-N-oxide