Iridium-catalyzed borylation of pyrene: irreversibility and the influence of ligand on selectivity

J Org Chem. 2015 Jan 2;80(1):661-5. doi: 10.1021/jo5024014. Epub 2014 Dec 16.

Abstract

The iridium-catalyzed borylation of pyrene, using 4,4'-dimethyl-2,2'-bipyridine as the ligand, in the presence of t-BuOK, gave a mixture of 2,4,7,9-tetrakis(Bpin)pyrene (c4) and its 2,4,7,10-isomer (m4) in a 2.2:1 ratio, and the selectivity of the Ir-catalyzed borylation of pyrene is kinetically determined and can be influenced to some extent by the nature of the ligand.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry
  • Catalysis
  • Iridium / chemistry*
  • Kinetics
  • Ligands
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Pyrenes / chemistry*
  • Pyridines / chemistry*

Substances

  • 4,4'-dimethyl-2,2'-bipyridine
  • Boron Compounds
  • Ligands
  • Organometallic Compounds
  • Pyrenes
  • Pyridines
  • Iridium
  • pyrene