• mariannefoo

C-N Cross-Coupling

Updated: Aug 5, 2019

#CN_coupling is an important class of reaction with a wide range of applications in pharmaceutical, agrochemical, and materials synthesis. In an #dual_catalysis approach, #nickel and #IrdFCF3ppy2dtbbpyPF6 were used to catalyze this C-N cross-coupling. The organic phenoxazine and dihydrophenazine PCs were shown effective in replacing the Ir PC. #PhenN_2Naph was demonstrated to couple secondary amines while #PhenO_1Naph_Biph was effective in coupling both primary (alkyl and aryl) and secondary amines.

#dihydrophenazine_publication #phenoxazine_publication

Du, Y.; Pearson, R. M.; Lim, C.-H.; Sartor, S. M.; Ryan, M. D.; Yang, H.; Damrauer, N. H.; Miyake, G. M., Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals. Chem. Eur. J. 2017, 23, 10962. Link

Papers related to C-N cross-coupling:

Corcoran, E. B.; Pirnot, M. T.; Lin, S.; Dreher, S. D.; DiRocco, D. A.; Davies, I. W.; Buchwald, S. L.; MacMillan, D. W. C., Aryl amination using ligand-free Ni(II) salts and photoredox catalysis. Science 2016, 353, 279. Link

Oderinde, M. S.; Jones, N. H.; Juneau, A.; Frenette, M.; Aquila, B.; Tentarelli, S.; Robbins, D. W.; Johannes, J. W., Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross-Coupling of Primary Aryl Amines with Aryl Halides. Angew. Chem. Int. Ed. 2016, 55, 13219. Link