Nickel-catalyzed alkyl-arylation of 3,3,3-trifluoropropene

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 NiCl2 center dot 6H(2)O as the catalyst and 4,4'-biMeO-bpy and PCy2Ph 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 beta-H and beta-F eliminations from TFP, rendering this strategy effective for the transformations of TFP into medicinal interest trifluoromethylated compounds. 3,3,3-Trifluoropropene is a cost-efficient precursor for the preparation of trifluoromethylated compounds, but limited methods for its efficient transformation have been reported. Here, nickel-catalyzed alkyl-arylation of 3,3,3-trifluoropropene with tertiary alkyl iodides and arylzinc reagents is achieved with high efficiency.

Automated summary

In this study, a nickel-catalyzed method for the alkyl-arylation of 3,3,3-trifluoropropene with tertiary alkyl iodides and arylzinc reagents is reported. This method overcomes previous challenges and is of significant importance for the transformation of 3,3,3-trifluoropropene into medicinal compounds.