Minisci reaction

It is a nucleophilic radical substitution to an electron deficient aromatic compound, most commonly the introduction of an alkyl group to a nitrogen containing heterocycle.

[3] The Minisci reaction often produces a mixture of regioisomers that can complicate product purification, but modern reaction conditions are incredibly mild, allowing a wide range of alkyl groups to be introduced.

The reaction allows for alkylation of electron deficient heterocyclic species which is not possible with Friedel-Crafts chemistry.

[1] The alkyl radical is also a 'soft' nucleophile and so is very unlikely to interact with any 'hard' electrophiles (carbonyl species for example) already present on the heterocycle,[9] which increases the functional group tolerance of the reaction.

The reaction has been the subject of much research in recent years, with a focus placed on improved reactivity towards a greater variety of heterocycles, increasing the number of alkylating reagents that can be used, and employing milder oxidants and acids.