Aza-fluorocyclization of nitrogen-containing unsaturated compounds

• Aza-fluorocyclization of unsaturated nitrogen-containing compounds is reviewed.
• Electrophilic N–F compounds are valuable reagents for preparation of organo-fluorine substances.
• Stereoselectivity of aza-fluorocyclization reactions is discussed

The aza-fluorocyclization of unsaturated nitrogen-containing compounds is reviewed. Syntheses of diverse fluorinated heterocycles by means of aza-fluorocyclization protocol are presented. The mechanism of the aza-fluorocyclization reactions, application of transition metals, and anionic phase-transfer catalysts are discussed. Advantages in the application of new strong electrophilic N–F reagents, including chiral [N–F]+ compounds soluble in non-polar organic solvents, are presented. The reactivity of various N–F reagents is validated. The influence of the nature of transition metals catalysts, fluorinating reagents and solvents on the stereoselectivity of the fluorocyclization is discussed. The asymmetric fluorination by application of chiral organic oxidants and anionic phase-transfer catalysts is presented. Recent development dealing with the application of metal-catalysis in the syntheses of heterocyclic compounds by aza-fluorocyclization protocol is reviewed. The review covers the literature from 2011 to June 2015. References to some earlier publications are given to compare the results which are discussed.

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