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

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F17%3A10360944" target="_blank" >RIV/00216208:11310/17:10360944 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.3390/catal7060167" target="_blank" >http://dx.doi.org/10.3390/catal7060167</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/catal7060167" target="_blank" >10.3390/catal7060167</a>

Result language

angličtina

Original language name

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

Original language description

Triethylammonium salts of phosphinoferrocene amidosulfonates with electron-rich dialkyphosphino substituents, R2PfcCONHCH2SO3(HNEt3) (4a-c), where fc = ferrocene-1,1 &apos;-diyl, and R = i-Pr (a), cyclohexyl (Cy; b), and t-butyl (c), were synthesized from the corresponding phosphinocarboxylic acids-borane adducts, R2PfcCO2H.BH3 (1a-c), via esters R2PfcCO2C6F5.BH3 (2a-c) and adducts R2PfcCONHCH2SO3(HNEt3).BH3 (3a-c). Compound 4b was shown to react with [Pd(mu-Cl)(eta-C3H5)]2 and AgClO4 to afford the zwitterionic complex [Pd(eta(3)-C3H5)(Cy2PfcCONHCH2SO3-kappa O-2,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 center dot CH2Cl2, 4b and 5b center dot CH2Cl2 were determined by single-crystal X-ray diffraction analysis. Compounds 4a-c and their known diphenylphosphino analogue, Ph(2)PfcCONHCH2SO3(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 = eta(2):eta(2)-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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10402 - Inorganic and nuclear chemistry

Project

<a href="/en/project/7F14392" target="_blank" >7F14392: Phosphine Ligands for Environmentally Friendly C-C Bond Forming Reactions</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Catalysts

ISSN

2073-4344

e-ISSN

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Volume of the periodical

7

Issue of the periodical within the volume

6

Country of publishing house

CH - SWITZERLAND

Number of pages

20

Pages from-to

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UT code for WoS article

000404380300001

EID of the result in the Scopus database

2-s2.0-85020431732