Different Performance of Two Isomeric Phosphinobiphenyl Amidosulfonates in Pd-Catalyzed Cyanation of Aryl Bromides
Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague, Czech Republic
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Academic Editor: Kei Manabe
Catalysts 2016, 6(12), 182; https://doi.org/10.3390/catal6120182
Received: 21 October 2016 / Revised: 16 November 2016 / Accepted: 21 November 2016 / Published: 25 November 2016
Abstract
A hydrophilic phosphinobiphenyl amidosulfonate, 2′-(dicyclohexylphosphino)-2- {[(sulfonatomethyl)amino]carbonyl}[1,1′-biphenyl], triethylammonium salt (L2), was prepared and, together with its isomer bearing the polar amido-sulfonate tag in the position 4 of the biphenyl scaffold (compound L1), evaluated as a supporting ligand in Pd-catalyzed cyanation of aryl bromides using K4[Fe(CN)6] as the non-toxic cyanide source. The less sterically demanding ligand L1 was found to form more active catalysts than the newly prepared compound L2. A catalyst formed in situ from palladium(II) acetate and L1 efficiently mediated cyanation of aryl bromides bearing electron-donating substituents but failed in the analogous reactions with electron-poor substrates. View Full-Text
Scheme 1
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Schulz, J.; Horký, F.; Štěpnička, P. Different Performance of Two Isomeric Phosphinobiphenyl Amidosulfonates in Pd-Catalyzed Cyanation of Aryl Bromides. Catalysts 2016, 6, 182.
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