Synthesis of aromatic ketones by Suzuki-Miyaura cross-coupling of acyl chlorides with boronic acids mediated by palladium catalysts deposited over donor-functionalized silica gel

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10293596" target="_blank" >RIV/00216208:11310/15:10293596 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.cattod.2014.06.017" target="_blank" >http://dx.doi.org/10.1016/j.cattod.2014.06.017</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.cattod.2014.06.017" target="_blank" >10.1016/j.cattod.2014.06.017</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of aromatic ketones by Suzuki-Miyaura cross-coupling of acyl chlorides with boronic acids mediated by palladium catalysts deposited over donor-functionalized silica gel

Popis výsledku v původním jazyce

Immobilized palladium catalysts prepared by deposition of palladium(II) acetate over silica gel functionalized with Si(CH2)(3)NHCH2Y donor groups (Y= SMe (1), NMe2 (2), PPh2 (3)) efficiently mediate cross-coupling of benzoyl chloride with benzeneboronicacid and its derivatives possessing electron-donating substituents. The presence of electron-withdrawing groups at the benzene ring decreases the yield of the coupling product while aliphatic acyl chlorides such as PhCH2CH2COCl and t-BuCoCl provide the coupling products in only poor yields. The course of the coupling reaction is very sensitive to the reaction conditions, the best results being achieved with potassium carbonate sesquihydrate as the base in dry toluene. The catalysts, which serve as the source of active metal, gradually loose their activity due to metal leaching and, mainly, decomposition of the solid support presumably by the action of the strong base present in the reaction system.

Název v anglickém jazyce

Synthesis of aromatic ketones by Suzuki-Miyaura cross-coupling of acyl chlorides with boronic acids mediated by palladium catalysts deposited over donor-functionalized silica gel

Popis výsledku anglicky

Immobilized palladium catalysts prepared by deposition of palladium(II) acetate over silica gel functionalized with Si(CH2)(3)NHCH2Y donor groups (Y= SMe (1), NMe2 (2), PPh2 (3)) efficiently mediate cross-coupling of benzoyl chloride with benzeneboronicacid and its derivatives possessing electron-donating substituents. The presence of electron-withdrawing groups at the benzene ring decreases the yield of the coupling product while aliphatic acyl chlorides such as PhCH2CH2COCl and t-BuCoCl provide the coupling products in only poor yields. The course of the coupling reaction is very sensitive to the reaction conditions, the best results being achieved with potassium carbonate sesquihydrate as the base in dry toluene. The catalysts, which serve as the source of active metal, gradually loose their activity due to metal leaching and, mainly, decomposition of the solid support presumably by the action of the strong base present in the reaction system.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CA - Anorganická chemie

OECD FORD obor

—

Projekt

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

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

Kód důvěrnosti údajů

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

Název periodika

Catalysis Today

ISSN

0920-5861

e-ISSN

—

Svazek periodika

243

Číslo periodika v rámci svazku

April

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

6

Strana od-do

128-133

Kód UT WoS článku

000347049900017

EID výsledku v databázi Scopus

2-s2.0-84927804575