4-Arylation of N-Acylamino- and Aminopyrazoles by the Suzuki-Miyaura Cross-Coupling Reaction

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F16%3A33160842" target="_blank" >RIV/61989592:15310/16:33160842 - isvavai.cz</a>

Výsledek na webu

<a href="http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600072/epdf" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600072/epdf</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201600072" target="_blank" >10.1002/ejoc.201600072</a>

Jazyk výsledku

angličtina

Název v původním jazyce

4-Arylation of N-Acylamino- and Aminopyrazoles by the Suzuki-Miyaura Cross-Coupling Reaction

Popis výsledku v původním jazyce

Halogenated aminopyrazoles have rarely been utilized in metal-catalysed cross-coupling reactions mainly due to the complexation of the aminopyrazoles to the metal center, which deactivates the catalyst. In this paper we reveal that the appropriate combination of palladium source and ligand enables efficient Suzuki-Miyaura cross-coupling reactions with even challenging substrates such as halogenated aminopyrazoles. The combination of Pd(OAc)2 and XPhos allowed efficient coupling of halogenated N-acetylaminopyrazoles, whereas XPhos Pd G2 was needed when unprotected aminopyrazoles were used. Generally, the halogenated aminopyrazoles underwent facile cross-coupling reactions with a range of aryl-, heteroaryl-, and styrylboronic acids and esters. The resulting biaryl, bisheteroaryl, or arylalkenyl derivatives were obtained in good-to-high isolated yields.

Název v anglickém jazyce

4-Arylation of N-Acylamino- and Aminopyrazoles by the Suzuki-Miyaura Cross-Coupling Reaction

Popis výsledku anglicky

Halogenated aminopyrazoles have rarely been utilized in metal-catalysed cross-coupling reactions mainly due to the complexation of the aminopyrazoles to the metal center, which deactivates the catalyst. In this paper we reveal that the appropriate combination of palladium source and ligand enables efficient Suzuki-Miyaura cross-coupling reactions with even challenging substrates such as halogenated aminopyrazoles. The combination of Pd(OAc)2 and XPhos allowed efficient coupling of halogenated N-acetylaminopyrazoles, whereas XPhos Pd G2 was needed when unprotected aminopyrazoles were used. Generally, the halogenated aminopyrazoles underwent facile cross-coupling reactions with a range of aryl-, heteroaryl-, and styrylboronic acids and esters. The resulting biaryl, bisheteroaryl, or arylalkenyl derivatives were obtained in good-to-high isolated yields.

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/LO1304" target="_blank" >LO1304: Podpora udržitelnosti Ústavu molekulární a translační medicíny</a><br>

Návaznosti

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

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Svazek periodika

2016

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

11

Strana od-do

2013-2023

Kód UT WoS článku

000374507400012

EID výsledku v databázi Scopus

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