Alkyl Aromatic Synthesis: Nucleophilic Alkyl Lithium Addition

Alkylated and, in particular, methylated polycyclic aromatic hydrocarbons and heteroaromatic compounds associated with increased coal utilization may be considerably more carcinogenic than the corresponding parent system.^1,2The availability of these alkylated compounds as standards for structural comparison or for biological testing is therefore of some importance. The report describes improvements on methodology for the synthesis of alkyl aromatic compounds by using a nucleophilic addition of an alkyl lithium (often enhanced by UV irradiation)^3-11in combination with the subsequent addition of iodine to conveniently regenerate the aromatic system (Scheme I, Table I).