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One‐Pot Domino Synthesis of Diarylalkynes/1,4‐Diaryl‐1,3‐diynes by [9,9‐Dimethyl‐4,5‐bis(diphenylphosphino)xanthene] (Xantphos)–Copper(I) Iodide–Palladium(II) Acetate‐Catalyzed Double Sonogashira‐Type Reaction
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-01-10 , DOI: 10.1002/adsc.201701128
Shaozhong Qiu 1 , Caiyang Zhang 1 , Rui Qiu 1 , Guodong Yin 1 , Jinkun Huang 2
Affiliation  

The low loading combination of the complex [9,9‐dimethyl‐4,5‐bis(diphenylphosphino)xanthene] (Xantphos)copper(I) iodide and simple ligand‐free palladium(II) acetate was found to be efficient for the domino synthesis of diarylalkynes by the reaction of aryl halides with trimethylsilylethynylene or bis(trimethylsilyl)acetylene in a single‐step procedure. The unsymmetrical diarylalkynes can be obtained through a one‐pot two‐step approach. The reactions of aryl bromides with 1,4‐bis(trimethylsilyl)butadiyne also furnished the corresponding 1,4‐diaryl‐1,3‐diynes in a similar fashion. This route to diarylalkynes and 1,4‐diaryl‐1,3‐diynes is complementary to previously reported synthetic procedures.

中文翻译:

[9,9-二甲基-4,5-双(二苯基膦基)氧杂蒽](Xantphos)-铜(I)碘化物-钯(II)的一锅多米诺合成二芳基炔烃/ 1,4-二芳基-1,3-二炔乙酸催化的双重Sonogashira型反应

发现复合物[9,9-二甲基-4,5-双(二苯基膦基)x吨](Xantphos)碘化铜(I)和简单的不含配体的乙酸钯(II)的低负荷组合对于多米诺骨牌有效一步法使卤代芳基与三甲基甲硅烷基乙炔或双(三甲基甲硅烷基)乙炔反应合成二芳基炔烃。不对称二芳基炔可以通过一锅两步法获得。芳基溴化物与1,4-双(三甲基甲硅烷基)丁二炔的反应也以类似的方式提供了相应的1,4-二芳基-1,3-二炔。这种通往二芳基炔烃和1,4-二芳基-1,3-二炔烃的方法是对先前报道的合成方法的补充。
更新日期:2018-01-10
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