Synthesis of Phosphanylferrocenecarboxamides Bearing Guanidinium Substituents and Their Application in the Palladium-Catalyzed Cross-Coupling of Boronic Acids with Acyl Chlorides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F17%3A10338364" target="_blank" >RIV/00216208:11310/17:10338364 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/ejic.201600461" target="_blank" >http://dx.doi.org/10.1002/ejic.201600461</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejic.201600461" target="_blank" >10.1002/ejic.201600461</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of Phosphanylferrocenecarboxamides Bearing Guanidinium Substituents and Their Application in the Palladium-Catalyzed Cross-Coupling of Boronic Acids with Acyl Chlorides

Popis výsledku v původním jazyce

Phosphanylferrocene donors bearing polar guanidinium substituents, namely acylguanidinium chloride, [Ph(2)PfcCONHC(NH2)NH2]Cl (1), and amidoguanidinium chloride, [Ph(2)PfcCONHCH(2)CH(2)NHC(NH2)NH2]Cl (2; fc = ferrocene-1,1-diyl), have been prepared and characterized. As functional phosphane donors, they were employed in the synthesis of Pd-II complexes bearing 2-[(dimethylamino)methyl-kappa N]phenyl-kappa C-1 (L-NC) and (3)-allyl supporting ligands, [(L-NC)PdCl(L-kappa P)] and [(eta(3)-C3H5)PdCl(L-P)] (L = 1 and 2), respectively. These defined complexes as well as their surrogates generated in situ from the respective palladium(II) precursor and the phosphanylferrocene ligand were evaluated as catalysts for the coupling of boronic acids with acyl chlorides to give ketones in an aqueous biphasic system. The coupling reaction proceeded best with a simple catalyst formed from Pd(OAc)(2) and ligand 2, which (at 0.2 mol-% Pd loading) produced substituted benzophenones from benzoyl chlorides and benzeneboronic acids in very good yields. These yields could then be further improved by a proper choice of the reaction partners. Analogous reactions involving aliphatic substrates generally afforded lower yields.

Název v anglickém jazyce

Synthesis of Phosphanylferrocenecarboxamides Bearing Guanidinium Substituents and Their Application in the Palladium-Catalyzed Cross-Coupling of Boronic Acids with Acyl Chlorides

Popis výsledku anglicky

Phosphanylferrocene donors bearing polar guanidinium substituents, namely acylguanidinium chloride, [Ph(2)PfcCONHC(NH2)NH2]Cl (1), and amidoguanidinium chloride, [Ph(2)PfcCONHCH(2)CH(2)NHC(NH2)NH2]Cl (2; fc = ferrocene-1,1-diyl), have been prepared and characterized. As functional phosphane donors, they were employed in the synthesis of Pd-II complexes bearing 2-[(dimethylamino)methyl-kappa N]phenyl-kappa C-1 (L-NC) and (3)-allyl supporting ligands, [(L-NC)PdCl(L-kappa P)] and [(eta(3)-C3H5)PdCl(L-P)] (L = 1 and 2), respectively. These defined complexes as well as their surrogates generated in situ from the respective palladium(II) precursor and the phosphanylferrocene ligand were evaluated as catalysts for the coupling of boronic acids with acyl chlorides to give ketones in an aqueous biphasic system. The coupling reaction proceeded best with a simple catalyst formed from Pd(OAc)(2) and ligand 2, which (at 0.2 mol-% Pd loading) produced substituted benzophenones from benzoyl chlorides and benzeneboronic acids in very good yields. These yields could then be further improved by a proper choice of the reaction partners. Analogous reactions involving aliphatic substrates generally afforded lower yields.

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/GA13-08890S" target="_blank" >GA13-08890S: Polární ferrocenové amidofosfinové ligandy pro katalytické aplikace</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

European Journal of Inorganic Chemistry

ISSN

1434-1948

e-ISSN

—

Svazek periodika

Neuveden

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

288-296

Kód UT WoS článku

000393404400014

EID výsledku v databázi Scopus

2-s2.0-85010304110