A novel synthesis of biaryl-containing macrocycles by a domino Miyaura arylboronate formation: intramolecular Suzuki reaction.
[reaction: see text] 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.
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Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France.
Zhu
J
J
D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D001896:Boron Compounds; D006571:Heterocyclic Compounds