Copper(Ⅰ)-Mediated Trifluoromethylthiolation Research

Introducing of trifluoromethylthio group into an organic compound would significantly alter its dipole moment, polarity, acidity, lipophicity, biological penetration, chemical and metabolic stability because of its strong electron-withdrawing, high lipophilicity and steady C-F bond. Therefore, compounds containing a trifluoromethylthiol group possess great potential application value in the field of medicines and agricultural chemicals. This thesis mainly reported efficient and convenient methods for the synthesis of allylic trifluoromethyl thioether and a-trifluoromethylthiolated ketones.In the second chapter, a novel, mild and efficient approach for the synthesis of allylic trifluoromethyl thioethers using DMF as solvent, CuSCN as copper salt, dry KF as base, S8 and TMSCF3 as trifluoromethylthiol source at 45℃ was developed. The obvious advantages of this method are the reaction could proceed smoothly with mild condition, good yield, and wide range of substrates as well as inexpensive and non-toxic reagents.In the third chapter, an efficient method for the synthesis of a-trifluoromethylthio-substituted ketones using DMF as solvent, CuI as copper salt, dry KF as base, S8 and TMSCF3 as trifluoromethylthiol source at room temperature was developed. The outstanding features of this approach are the reaction could proceed with mild condition, short reaction time and readily available and cheap reagents.