Trifluoromethyl-Substituted Selenium Ylide: A Broadly Applicable Electrophilic Trifluoromethylating Reagent

Qilong Shen shows the application potential of trifluoromethyl-substituted selenium ylide.

Many electrophilic trifluoromethylating reagents have emerged in the past three decades. Among them, Umemoto’s reagent and Togni’s reagent are two of the most studied examples due to their high reactivity and broad substrate scope. Nevertheless, new, highly reactive and easily prepared electrophilic trifluoromethylating reagents are still urgently needed.
Recently, the group of Professor Qilong Shen at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (P. R. of China) discovered that monofluoromethyl- or difluoromethyl-substituted sulfonium ylides, which could be synthesized from 4-nitrophenylthiol in two steps, were highly active and reacted with a broad range of nucleophiles under mild conditions. In their new study they replaced trifluoromethyl-substituted sulfonium ylide with the selenium analogue to significantly increase the reactivity.

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