Highly Efficient Pd/Tetraphosphine Catalytic System for Copper-Free Sonogashira Reactions of Aryl Bromides with Terminal Alkynes |
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Authors: | Tao Yi Min Mo Hai-Yan Fu Rui-Xiang Li Hua Chen Xian-Jun Li |
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Affiliation: | (1) Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, People’s Republic of China; |
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Abstract: | Abstract In this study, an easily synthesized polydentate ligand N,N,N’,N’-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine (1) in combination with [Pd(C3H5)Cl]2 was found to be an active catalyst in copper-free Sonogashira reactions. Most substrates, including steric hindered phenyl bromides and heteroaryl bromides, could couple efficiently with terminal alkynes in the presence of low catalyst loading (0.1 mol%) and this catalytic system showed excellent functional group tolerance. The influence of water in this system was also preliminarily investigated via 31P NMR in situ; that is, appropriate water favors the reaction while excess hindered this reaction. |
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