可见光催化下三氟甲基酮的选择性合成

Selective Synthesis of Trifluoromethyl Ketone by Visible-light Catalysis

三氟甲基因其强吸电子性、亲脂性,将其引入到有机化合物中能够显著改变化合物的酸性、偶极距、极性、亲脂性以及其化学和代谢稳定性。在可见光作用下,以曙红Y(esoin Y)作为光催化剂,利用三氟甲基亚磺酸钠作为三氟甲基试剂,实现了腙类化合物C-H键的三氟甲基化,利用腙实现了羰基化合物的极性反转,高效的实现了三氟甲基酮(TFMK)的合成,底物适用范围广,反应条件温和。

Introducing trifluoromethyl into organic compounds can significantly change the acidity,dipole polarity,polarity,lipophilicity and chemical and metabolic stability of the compounds because of its strong electron-withdrawing activity and lipophilicity. Trifluoromethyl compounds have been widely used in the fields of medicine,pesticides and materials. Trifluoromethyl ketone is a class of particularly important compounds in many molecules containing trifluoromethyl,which can be used as the enzyme inhibitors with strong biological activities as well as the important intermediate for the synthesis of other trifluoromethyl derivatives. Based on the preliminary work,the synthesis of trifluoromethyl ketone was studied with carbonyl compounds as substrate under the irradiation of visible light catalyzed by eosin Y. The reaction system was optimized through expanding the scope of trifluoromethyl reagents. The reaction area selectivity was studied through the introduction of guide groups.