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Catalysts 2017, 7(6), 167; doi:10.3390/catal7060167

Synthesis, Structural Characterization and Catalytic Evaluation of Anionic Phosphinoferrocene Amidosulfonate Ligands

Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague, Czech Republic
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Academic Editor: Ioannis D. Kostas
Received: 20 April 2017 / Revised: 19 May 2017 / Accepted: 19 May 2017 / Published: 24 May 2017
(This article belongs to the Special Issue Suzuki–Miyaura Cross-Coupling Reaction and Potential Applications)
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Abstract

Triethylammonium salts of phosphinoferrocene amidosulfonates with electron-rich dialkyphosphino substituents, R2PfcCONHCH2SO3(HNEt3) (4ac), where fc = ferrocene-1,1′-diyl, and R = i-Pr (a), cyclohexyl (Cy; b), and t-butyl (c), were synthesized from the corresponding phosphinocarboxylic acids-borane adducts, R2PfcCO2H·BH3 (1ac), via esters R2PfcCO2C6F5·BH3 (2ac) and adducts R2PfcCONHCH2SO3(HNEt3)·BH3 (3ac). Compound 4b was shown to react with [Pd(μ-Cl)(η-C3H5)]2 and AgClO4 to afford the zwitterionic complex [Pd(η3-C3H5)(Cy2PfcCONHCH2SO32O,P)] (5b), in which the amidosulfonate ligand coordinates as a chelating donor making use of its phosphine moiety and amide oxygen. The structures of 3b·CH2Cl2, 4b and 5b·CH2Cl2 were determined by single-crystal X-ray diffraction analysis. Compounds 4ac and their known diphenylphosphino analogue, Ph2PfcCONHCH2SO3(HNEt3) (4d), were studied as supporting ligands in Pd-catalyzed cyanation of aryl bromides with K4[Fe(CN)6] and in Suzuki–Miyaura biaryl cross-coupling performed in aqueous reaction media under mild reaction conditions. In the former reaction, the best results were achieved with a catalyst generated from [PdCl2(cod)] (cod = η22-cycloocta-1,5-diene) and 2 equiv. of the least electron-rich ligand 4d in dioxane–water as a solvent. In contrast, the biaryl coupling was advantageously performed with a catalyst resulting from palladium(II) acetate and ligand 4a (1 equiv.) in the same solvent. View Full-Text
Keywords: ferrocene ligands; phosphines; sulfonates; aqueous catalysis; Suzuki–Miyaura reaction; cyanation; palladium ferrocene ligands; phosphines; sulfonates; aqueous catalysis; Suzuki–Miyaura reaction; cyanation; palladium
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MDPI and ACS Style

Schulz, J.; Horký, F.; Císařová, I.; Štěpnička, P. Synthesis, Structural Characterization and Catalytic Evaluation of Anionic Phosphinoferrocene Amidosulfonate Ligands. Catalysts 2017, 7, 167.

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