Palladium-Catalyzed C4,C5-Diarylation of Isoxazole-3-carboxylate by Double C–H Bond Functionalization

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-11-04 DOI:10.1002/ejoc.202401036
Rabeb Ben Romdhane, Linhao Liu, Ridha Ben Salem, Henri Doucet
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Abstract

The Pd-catalyzed C4-arylation of 3,5-disubstituted isoxazoles via C-H bond functionalization has been largely described. By contrast, the reactivity of isoxazoles in C-H bond functionalization with both unsubstituted C4 and C5 positions remains largely unexplored. Herein, we report on the reactivity in Pd-catalyzed double C-H bond arylation of an isoxazole with unsubstituted C4 and C5 positions. Conditions for the palladium-catalyzed direct C4,C5-diarylation of ethyl isoxazole-3-carboxylate using aryl bromides as the aryl source are reported. This procedure tolerates several useful substituents on the aryl bromide such as nitrile, acetyl, formyl, benzoyl, alkoxycarbonyl, chloro, fluoro, trifluoromethyl, trifluoromethoxy, cyanomethyl,tertbutyl and methoxy at para- and meta-positions. Conversely, with ortho-substituted aryl bromides, mixtures of mono- and di-arylated isoxazoles were generally obtained. This methodology provides a simple one pot access to a wide variety of C4,C5-diarylated isoxazoles from commercially available substrates allowing to modify easily their biological properties.
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钯催化双 C-H 键官能化异恶唑-3-羧酸酯的 C4、C5-二芳基化反应
通过 C-H 键官能化,Pd 催化 3,5 二甲基异噁唑的 C4 芳基化反应已被广泛描述。相比之下,异噁唑与未取代的 C4 和 C5 位的 C-H 键官能化反应性在很大程度上仍未得到探索。在此,我们报告了钯催化未取代 C4 和 C5 位的异噁唑双 C-H 键芳基化的反应性。报告了以芳基溴化物为芳基源,钯催化异噁唑-3-羧酸乙酯直接发生 C4、C5-二芳基化反应的条件。该过程可容忍芳基溴上的几个有用取代基,如腈、乙酰基、甲酰基、苯甲酰基、烷氧羰基、氯、氟、三氟甲基、三氟甲氧基、氰甲基、叔丁基和对位和偏位的甲氧基。相反,使用正交取代的芳基溴,通常会得到单芳基和二芳基异噁唑的混合物。这种方法提供了一种简单的一锅式方法,可从市售底物中获得多种 C4、C5-二芳基化异噁唑,从而轻松改变它们的生物特性。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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