Synthesis of Trifluoromethyl-Substituted Allenols via Catalytic Trifluoromethylbenzoxylation of 1,3-Enynes

Posted on 2023-01-25 - 13:37
Allenol has been identified as a versatile building block for organic synthesis, and numerous efforts have been made to synthesize and apply allenol. However, limited efforts have been made to obtain a trifluoromethyl-substituted allenol. Here, by using a readily available 1,3-enyne as the starting material, a copper-catalyzed trifluoromethylbenzoxylation process was developed for efficient synthesis of trifluoromethyl-substituted allenols using Togni-II reagent as the reaction partner. Triple roles of the Togni-II reagent, including as the source of the trifluoromethyl group, as the source of the hydroxyl group, and as the oxidant, were elucidated in this transformation. Moreover, late-stage diversification was performed, which revealed the application potential of trifluoromethyl-substituted allenols for the preparation of various trifluoromethyl-substituted compounds.

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Li, Songrong; Yang, Wenwen; Shi, Junjie; Dan, Tingting; Han, Yujie; Cao, Zhi-Chao; et al. (2023): Synthesis of Trifluoromethyl-Substituted Allenols via Catalytic Trifluoromethylbenzoxylation of 1,3-Enynes. ACS Publications. Collection. https://doi.org/10.1021/acscatal.2c04978
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