三氟甲基化
三氟甲基
烯烃
化学
炔烃
反应性(心理学)
烯烃纤维
背景(考古学)
组合化学
产量(工程)
表面改性
光化学
催化作用
药物化学
有机化学
材料科学
冶金
替代医学
古生物学
物理化学
病理
生物
医学
烷基
作者
Shuo Guo,Deyaa I. AbuSalim,Silas P. Cook
标识
DOI:10.1002/anie.201905247
摘要
Abstract Modifying the electronic properties of olefins is the quintessential approach to tuning alkene reactivity. In this context, the exploration of trifluoromethyl groups as divergent electronic modifiers has not been considered. In this work, we describe a copper‐mediated 1,2‐(bis)trifluoromethylation of acetylenes to create E ‐hexafluorobutenes ( E ‐HFBs) under blue light in a single step. The reaction proceeds with high yield and E / Z selectivity. Since the alkyne captures two trifluoromethyl groups from each molecule of bpyCu(CF 3 ) 3 , mechanistic studies were conducted to illuminate the role of the reactants. Interestingly, E ‐HFBs exhibit remarkable stability to standard olefin functionalization reactions in spite of the pendant trifluoromethyl groups. This finding has significant implications for medicine, agroscience, and materials.
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