In this article we describe an efficient approach for the synthesis of cyclic diaryliodonium salts. The method is based on benzyl alcohols as starting materials and consists of an Friedel-Crafts-arylation/oxidation sequence. Besides a deep optimization, particluar focusing on the choice and ratios of the utilized Bronsted-acids and oxidants, we explore the substrate scope of this transformation. We also discuss an interesting isomerism of cyclic iodonium salts substituted with aliphatic substituents at the bridge head carbon. <br>
Synthesis and Radical Cyclization of 2-(β-Haloacyl)-1,2-dihydroisoquinolines by Means of Tin Hydride. One-Pot Synthesis of Benzo[f]indolizidine Systems from Isoquinolines