Studies on the radical addition reaction of perfluoroalkyl iodides with 2,3-allenols and the Pd-catalyzed kinetic resolution via Sonogashira coupling reaction
2011
Ma, Zhichao | Zeng, Rong | Fu, Chunling | Ma, Shengming
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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