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.R.; Batsanov, A.S.; Monkman, A.P.

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.

Citation

Tavasli, M., Bettington, S., Bryce, M., Batsanov, A., & Monkman, A. (online). 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. Synthesis: Journal of Synthetic Organic Chemistry, 1619-1624

• Journal Article Type: Article
• Journal: Synthesis : journal of synthetic organic chemistry.
• Print ISSN: 0039-7881
• Electronic ISSN: 1437-210X
• Publisher: Thieme Gruppe
• Peer Reviewed: Peer Reviewed
• Issue: 10
• Pages: 1619-1624
• Public URL: https://durham-repository.worktribe.com/output/1568722