Regioselective transformation of terminal and internal alkynes into α,α-difluoro ketones under mild conditions

作者：Lin, Chuyuan; Lin, Zhenyuan; Ye, Zhenying; Chen, Lu^*; Li, Yibiao; Shen, Chengshuo^*; Zhang, Min^*

来源：2022, 110: 154197.

DOI：10.1016/j.tetlet.2022.154197

• Alkynes
• alpha,alpha-Difluoroketones
• DFT calculations
• Selectfluor

Here, we report a facile approach for divergent synthesis of aryl alpha,alpha-difluoroketones from both terminal and internal arylalkynes by employing Selectfluor as the fluorine-source. DFT calculations of this transformation reveal that the products are formed via electrophilic fluorination of the C-C triple bond. In comparison with the existed approaches allowing the preparation of limited alpha,alpha-difluoroketones, the present work enriches the capabilities of synthesizing different alpha-fluorinated arylketones, and offers a fundamental basis for further development of fluorinated products including drugs and functional materials due to the significant importance of fluorinated ketones in organic synthesis. Moreover, the metal-free conditions in conjunction with the use of cost-effective H2O and better functional group tolerance highlight the practicality of the developed chemistry.