Palladium-on-Carbon-Catalyzed Coupling of Nitroarenes with Phenol: Biaryl Ether Synthesis and Evidence of an Oxidative-Addition-Promoted Mechanism,European Journal of Organic Chemistry

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Palladium-on-Carbon-Catalyzed Coupling of Nitroarenes with Phenol: Biaryl Ether Synthesis and Evidence of an Oxidative-Addition-Promoted Mechanism
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2017-06-14 02:35:33 , DOI: 10.1002/ejoc.201700639
Tahshina Begum ₁ , Manoj Mondal ₂ , Manash Protim Borpuzari ₁ , Rahul Kar ₁ , Pradip K. Gogoi ₁ , Utpal Bora ₂

Affiliation

Nucleophilic substitution in nitroarenes to form biaryl ethers is of fundamental importance in organic synthesis. Under non-catalytic conditions, this can occur if highly activated nitroarenes are used or if the nucleophile is activated by a strong stoichiometric base. We established a new method involving the use of a ligand-free palladium-on-carbon (Pd/C) catalyst for the cross-coupling of activated nitroarenes with relatively non-nucleophilic phenol derivatives, including naphthol, in the absence of harsh bases. Control experiments, hot filtration, the three-phase test, and inductively coupled plasma atomic emission spectroscopy analysis revealed that the catalysis proceeded through an usual oxidative addition step of the nitroarene to Pd/C, which resulted in the release of active palladium particles having extremely high catalytic activity. DFT calculations revealed the origin of the selectivity of the activated nitroarenes.

中文翻译：

钯在碳上催化硝基芳烃与苯酚的偶联：联芳基醚的合成和氧化加成促进机理的证据

在硝基芳烃中形成双芳基醚的亲核取代在有机合成中至关重要。在非催化条件下，如果使用高度活化的硝基芳烃或亲核试剂被强化学计量的碱活化，则会发生这种情况。我们建立了一种新方法，该方法涉及在没有苛刻碱的情况下，使用无配体的碳载钯（Pd / C）催化剂将活化的硝基芳烃与相对非亲核的苯酚衍生物（包括萘酚）进行交叉偶联。对照实验，热过滤，三相试验和电感耦合等离子体原子发射光谱分析表明，催化过程是通过通常的硝基芳烃氧化加成步骤至Pd / C进行的，从而释放出活性钯颗粒，其活性极强。高催化活性。

更新日期：2017-06-14

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