Abstract
A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the rates of the reactions. Interestingly, differences in reactivity were observed when a well-defined [LCuCF3] complex was employed directly or generated in situ from precursors by published reports. Relative reactivities were also found to highly dependent on the nature of the iodoarenes.
Highlights
Fluorinated molecules that bear the trifluoromethyl group have great importance in the life sciences and materials fields as well as discovery chemistry in general [1,2,3]
Sporadic examples of trifluoromethylation ‘catalysis’ using copper have been observed [4,5,6,7,8,9], but these reactions typically only work for aryl iodides and have a low substrate scope, low turn-over values, and/or involve decarboxylation reactions at high temperatures
Because the phenanthroline-based system described as B1 (Scheme 1) is the most widely used reagent for trifluoromethylations, we modeled our “standard” comparative conditions similar to those reported by Hartwig in 2011 [12]
Summary
Fluorinated molecules that bear the trifluoromethyl group have great importance in the life sciences and materials fields as well as discovery chemistry in general [1,2,3]. Conditions that generate “ligandless” [CuCF3] (D1, for example) are amenable for the trifluoromethylation of aryl iodides [15], but it is unclear how the reactivity profile of the ligandless complex compares to systems A–C described in Scheme 1.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
