Practical syntheses of N-hexylcarbazol-2-yl- and -3-yl-boronic acids, their cross-coupled products and a derived tris-cyclometalated (pyridin-2-yl)carbazole iridium(III) complex


TAVASLI M. , Bettington S., Bryce M., Batsanov A., Monkman A.

SYNTHESIS-STUTTGART, no.10, pp.1619-1624, 2005 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: Issue: 10
  • Publication Date: 2005
  • Doi Number: 10.1055/s-2005-865307
  • Title of Journal : SYNTHESIS-STUTTGART
  • Page Numbers: pp.1619-1624
  • Keywords: carbazole, boronic acid, fluorene, cross-coupling reaction, cyclometalating ligands, iridium complex, LADDER OLIGO(P-ANILINE)S, MICROWAVE IRRADIATION, CARBAZOLE TRIMERS, ROUTE, BROMINATION, DIINDOLOCARBAZOLES, SUBSTITUENTS, COPOLYMERS, POLYMERS

Abstract

The syntheses of N-hcxylcarbazol-2-yl- and -3-yl-boronic acids (1 and 2) are described on a ca. 7 g scale, starting from commercially available 2,5-dibromonitrobenzene (4) and carbazole (11), respectively. Compounds I and 2 underwent efficient palladium-catalyzed cross-coupling reactions under Suzuki-Miyaura conditions to yield products 17, 18 and 20. Compound 18 reacted with IrCl3 to give the tris-cyclometalated (pyridin-2-yl)carbazole iridium(III) complex 21, the X-ray crystal structure of which is reported.