Tetrakis(9H-carbazol-9-yl)benzene-1,3-dicarbonitrile

CAS 1416881-52-1, Cat. No EN300-6487157

Ligang for organic photocatalysis

2,4,5,6-Tetra(carbazol-9-yl)isophthalonitrile, also known as 4CzIPN, is a donor-acceptor chromophore and efficient metal-free photoredox catalyst for organic synthesis. The compound is a powder that is stable in the fridge for an extended period and easy to handle. It is a popular catalyst in photoredox/Ni dual catalytic C(sp³)−C(sp²) cross-couplings. 4CzIPN demonstrates exceptional efficacy in the arylation of a wide range of substrates. Besides other reactions, it enables α-arylation of tertiary alkylamines, replacement of the carboxylic group in α-amino acids, and couplings with trifluoroborates with good yields. Only a catalytic amount of the 4CzIPN is required. Notably, synthesis can be performed under mild conditions even with blue LED light without the need for harsh UV irradiation.

Synonyms: 4CzIPN, 2,4,5,6-Tetra(carbazol-9-yl)isophthalonitrile, 2,4,5,6-tetra(carbazol-9-yl)benzene-1,3-dicarbonitrile

Selected publication

1. Organic Photoredox Catalysis.

Romero N. A.; Nicewicz D. A. Chem Rev 2016, 116 (17), 10075–10166. DOI: 10.1021/acs.chemrev.6b00057

2. 1,3-Benzenedicarbonitrile, 2,4,5,6-Tetra-9 H -Carbazol-9-Yl-.

Lu J.; Gui R.; Zhang J. Encyclopedia of Reagents for Organic Synthesis 2017, 1–2. DOI: 10.1002/047084289X.rn02068

3. Single-Electron Transmetalation in Organoboron Cross-Coupling by Photoredox/Nickel Dual Catalysis.

Tellis J. C.; Primer D. N.; Molander G. A. Science 2014, 345 (6195), 433–436. DOI: 10.1126/science.1253647