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

作者：Songrong Li, Wenwen Yang, Junjie Shi, Tingting Dan, Yujie Han, Zhi‐Chao Cao, Mingyu Yang · 发表于：ACS Catalysis · 年份：2023 · DOI：10.1021/acscatal.2c04978 · 被引用次数：30 · 研究领域：Fluorine in Organic Chemistry、Catalytic C–H Functionalization Methods、Catalytic Alkyne Reactions

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.