Defluorinative Alkylation of Trifluoromethyl Alkenes with Soft Carbon Nucleophiles Enabled by a Catalytic Amount of Base

Ya Gao, Wei Qin, Ming-Qing Tian, Xuefei Zhao,* and Xu-Hong Hu*

Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, People’s Republic of China

Abstract: Direct manipulation of readily accessible trifluoromethyl alkenes (TAs) represents an attractive approach to the preparation of diversified fluorine-containing compounds. In this study, defluorinativealkylation reactions of TAs with a broad array of soft carbon nucleophiles have been documented. Nucleophilic substitutions occur enabled by a catalytic amount of base, providing access to tertiary alkyl substituted gem-difluoroalkenes and 2-fluoro-4H-pyrans. By extending the nucleophiles to silyl enol ethers, defluorination can be achieved in the absence of base to give gemdifluoroalkenes. This process, which eliminates the requirement of organometallic reagents, transition metals, or strong bases for the C- F bond cleavage, is applicable to late-stage modification of complex molecules.

Adv. Synth. Catal. 2022, 364, 2241-2247 (2022年影响因子：5.981)

论文链接：https://onlinelibrary.wiley.com/doi/10.1002/adsc.202200328

被《今日论文》报道评述：https://mp.weixin.qq.com/s/ikM4Usn9oADhL6HtE4Yedw