Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2‐(2‐Bromoprop‐2‐enyl)cyclohexanone Derivatives via ‘ Intramolecular Unsaturation Transfer ’

Alkylbenzenes are synthesized for the first time from aliphatic hydrocarbons via an one pot, transition metal‐free coupling approach under basic conditions. The method consists of two steps: condensation of 2‐bromoprop‐2‐enyl‐ or 2‐propargylcyclohexanone with alcohols, amines, or amino alcohols, followed by base treatment ( Scheme 1 ). Phenolic ethers and N ‐phenylated polyalkyl aromatic compounds are shown to be in the scope of the demonstrated reaction ( Table ). The proposed mechanism suggests that the unsaturation in another part of the molecule (propargyl‐group equivalent) is transferred into the cyclohexane ring to yield a benzene ring through a series of prototropic shifts.