Cyclodehydration of Fluorinated Diols Using the Mitsunobu Reaction: Highly Efficient Synthesis of Trifluoromethylated Cyclic Ethers

Synthesis of trifluoromethylated cyclic ethers has been achieved via the Mitsunobu cyclodehydration of fluorinated diols with high efficacy. The methodology is found to be widely applicable to the synthesis of cyclic ethers with varying ring size (3-7) from fluorinated diols of differing acidities and steric demands. Cyclic ethers with considerable ring strain can be achieved in moderate yields by this protocol. The methodology is suitable for both primary and secondary alcohols as well as benzylic and aliphatic alcohols as electrophiles to afford the corresponding products in moderate to good yields.