A novel synthesis of biaryl-containing macrocycles by a domino miyaura arylboronate formation: Intramolecular Suzuki reaction

[GRAPHICS] A novel macrocyclization procedure is developed on the basis of a domino process. Thus, treatment of linear diiodide 11 under defined conditions gave the 15-membered m,m-cyclophane 12 via aryl-aryl bond formation. Two distinct cross coupling manifolds, Miyaura's arylboronic ester synthesis and intramolecular Suzuki reaction, proceed in an ordered fashion. Concentration is an important factor for the success of this process.