Studies on the radical addition reaction of perfluoroalkyl iodides with 2,3-allenols and the Pd-catalyzed kinetic resolution via Sonogashira coupling reaction |
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| Authors: | Zhichao MaRong Zeng Chunling FuShengming Ma |
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| Institution: | Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China |
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| Abstract: | A radical addition reaction promoted by Na2S2O4 of perfluoroalkyl iodides with 2,3-allenols affording E/Z mixtures of 3-iodo-4-perfluoroalkyl-substituted allylic alcohols has been studied. Kinetic resolution with Sonogashira coupling reaction was applied to afford the Z isomer of 3-iodo-4-perfluoroalkyl-substituted allylic alcohol (Z-3) and the E isomer of conjugated enynic diols (E-5) in 39-52% and 22-40% yields, respectively. |
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| Keywords: | Allenol Kinetic resolution Radical addition |
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