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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.

Authors

M. Tavasli

S. Bettington

A.S. Batsanov



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. (2005). 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
Publication Date 2005-07
Journal Synthesis : journal of synthetic organic chemistry.
Print ISSN 0039-7881
Publisher Thieme Gruppe
Peer Reviewed Peer Reviewed
Issue 10
Pages 1619-1624