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Catalysts 2016, 6(12), 182; doi:10.3390/catal6120182

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
Received: 21 October 2016 / Revised: 16 November 2016 / Accepted: 21 November 2016 / Published: 25 November 2016
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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
Keywords: cross-coupling reactions; palladium; biphenyl phosphines; cyanation; aqueous catalysis cross-coupling reactions; palladium; biphenyl phosphines; cyanation; aqueous catalysis
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Scheme 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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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