Allylic C-H amination is one of the highly useful processes for the direct preparation of organonitrogen compounds. A catalytic method for selective allylic C-H amination of dienes and trienes using arylhydroxylamines is developed. This iron-catalyzed approach involves in situ generation of activated nitrosoarenes, which in turn react with dienes/trienes in a selective manner to give their corresponding aminomethyl dienes/trienes. The catalyst plays a key role to accelerate the ene-reaction by hindering the possible hetero Diels-Alder reaction via selective activation of diene and nitrosoarene. Regioselectivity depends on both the substitution pattern and electronic factors of the substrate. This method is simple and useful for the preparation of functionalized polyenes. Method development and mechanistic aspects of the reaction will be presented. 

Iron-catalyzed selective allylic C-H amination of substituted 1,3-dienes

247th National Meeting (2014)

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