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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10402 - Inorganic and nuclear chemistry

Projekt

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

Návaznosti

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

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

Catalysts

ISSN

2073-4344

e-ISSN

—

Svazek periodika

7

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

20

Strana od-do

—

Kód UT WoS článku

000404380300001

EID výsledku v databázi Scopus

2-s2.0-85020431732