镍催化的3,3,3-三氟丙烯的烷基-芳基化反应
Nickel-catalyzed alkyl-arylation of 3,3,3-trifluoropropene.
作者信息
Xu Chang, Wang Ming-Kuan, Zhang Shu, Zhang Xingang
机构信息
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
The Yangtze Delta Region Institute (Huzhou), University of Electronic Science and Technology of China, Huzhou, 313001, China.
出版信息
Commun Chem. 2022 Mar 22;5(1):41. doi: 10.1038/s42004-022-00659-7.
Owing to the versatile synthetic utility of its carbon-carbon double bond, low-cost industrial chemical 3,3,3-trifluoropropene (TFP) represents one of the most straightforward and cost-efficient precursors to prepare trifluoromethylated compounds. However, only limited methods for the efficient transformations of TFP have been reported so far. Here, we report a nickel-catalyzed dicarbofunctionalization of TFP. The reaction uses inexpensive NiCl·6HO as the catalyst and 4,4'-biMeO-bpy and PCyPh as the ligands, allowing the alkyl-arylation of TFP with a variety of tertiary alkyl iodides and arylzinc reagents in high efficiency. This nickel-catalyzed process overcomes the previous challenges by suppressing β-H and β-F eliminations from TFP, rendering this strategy effective for the transformations of TFP into medicinal interest trifluoromethylated compounds.
由于其碳 - 碳双键具有广泛的合成用途，低成本工业化学品3,3,3 - 三氟丙烯（TFP）是制备三氟甲基化化合物最直接且成本效益最高的前体之一。然而，迄今为止，仅报道了有限的有效转化TFP的方法。在此，我们报道了一种镍催化的TFP双碳官能化反应。该反应使用廉价的NiCl·6H₂O作为催化剂，4,4'-联甲氧基联吡啶和三环己基苯基膦作为配体，能使TFP与多种叔烷基碘化物和芳基锌试剂高效地进行烷基 - 芳基化反应。这种镍催化过程通过抑制TFP的β - H和β - F消除克服了先前的挑战，使得该策略对于将TFP转化为具有药用价值的三氟甲基化化合物有效。
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