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

Org Lett. 2000 Nov 2;2(22):3477-80. doi: 10.1021/ol006520g.

Abstract

[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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry
  • Drug Design
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Boron Compounds
  • Heterocyclic Compounds