AbstractAn efficient and facile methodology for the synthesis of α‐arylated N‐heteroarenes was developed under aerobic conditions by means of ultrasound assistance, as well as conventional heating via a direct α‐arylation protocol employing Imidazolium based ionic liquids serving as both acid promoter and solvent. Structurally diverse N‐heteroarenes and 1‐aryltriazenes were evaluated for this reaction. This methodology has successfully provided a synthetic handle for various electron‐rich and electron‐deficient arylated N‐heteroarenes under metal and/or peroxide free conditions in good to excellent yields. The total synthesis of the known oxoisoaporphine class of alkaloids Menisporphine & Daurioxoisoporphine C was successfully accomplished using the current methodology as a key step in the total synthesis.