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, sa.10, ss.1619-1624, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: Sayı: 10
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1055/s-2005-865307
  • Dergi Adı: SYNTHESIS-STUTTGART
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1619-1624
  • Anahtar Kelimeler: 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
  • Bursa Uludağ Üniversitesi Adresli: Hayır

Özet

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.