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Copper-Catalyzed N-Arylation of Pyranoquinolinones with Boronic Acids at Room Temperature without Ligand

Wei Gao,Fang Gao,Haikuan Yang,Zongde Wang,Yaru Huang

Pyranoquinolinones synthesized from citral were used for Cu-catalyzedN-arylation with a wide range of arylboric acids. The reaction proceeded well with a broad substrate scope, providing a direct way to access highly functional pyranoquinolinone core structure derivatives in yields of up to 80%. Compared to citral, the compounds we obtained have a much better inhibitory effect on HeLa cervical cancer cells, and compound3phas an IC50value of 4.6 μM, lower than cisplatin’s 5.9 μM.Keywords:citral;pyranoquinolinone;N-arylation

研究领域: 有机化学 · 药物化学 · 癌症研究

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CHINESE JOURNAL OF CATALYSIS · 2013 · IF 1.304

Substrate-promoted copper-catalyzed N-arylation of amino alcohols with aryl iodides in water

Ming Jin,Dan Zhao,Guozhen He,Yao Tong,Shiqing Han

An efficient method has been developed for the N -arylation of a variety of water-soluble amino alcohols (1.2 mmol) with aryl iodides (1.0 mmol) in water under CuI-catalyzed conditions. The reaction was conducted via substrate-promoted action and did not require an additional ligand or phase-transfer catalyst, and afforded the desired N -aryl amines in acceptable to excellent yields (64%–93%) under mild reaction conditions with a small excess of the amino alcohol.

研究领域: 有机化学 · 合成化学

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NEW JOURNAL OF CHEMISTRY · 2013 ·Vol. 37 ·期 8 ·2537-2540 · IF 2.966

Aqueous copper-catalyzed N-arylation of indoles: the surfactant strategy

Songbai Liu,Jiahui Zhou

Surfactants have long been underestimated in synthetic organic chemistry despite their great potential in promoting solubility, reactivity and selectivity in metal-mediated cross-couplings. In this study the strategy of surfactant promotion was exemplified in copper-catalyzed N-arylation of indoles in water. The different effects of surfactants during the coupling reaction were first explored. The superior promoting effect of the natural zwitterionic surfactant, betaine, was found and attributed to the capability of the formed complex to stabilize the copper intermediate in the catalytic transformation and facilitate transportation of the reactants. The concept of surfactant promotion through complexation is valuable in metal-mediated cross-couplings. This method also exhibited good recycling ability. This study will greatly facilitate exploration of surfactant promotion in metal-mediated cross-couplings.

研究领域: 有机化学 · 合成化学

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Copper-Catalyzed N-Arylation of Pyranoquinolinones with Boronic Acids at Room Temperature without Ligand

Substrate-promoted copper-catalyzed N-arylation of amino alcohols with aryl iodides in water

Aqueous copper-catalyzed N-arylation of indoles: the surfactant strategy