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The TeF 5 group is significantly underexplored as a highly fluorinated substituent on an organic framework, despite it being a larger congener of the acclaimed SF 5 group. In fact, only one aryl-TeF 5 compound (phenyl-TeF 5 ) has been reported to date, synthesized using XeF 2 . Our recently developed mild TCICA/KF approach to oxidative fluorination provides an affordable and scalable alternative to XeF 2 . Using this method, we report a scope of extensively characterized aryl-TeF 5 compounds, along with the first SC-XRD data on this compound class. The methodology was also extended to the synthesis and structural study of heretofore unknown aryl-TeF 4 CF 3 compounds. Additionally, preliminary reactivity studies unveiled some inconsistencies with previous literature regarding phenyl-TeF 5 . Although our studies conclude that the arene-based TeF 5 (and TeF 4 CF 3 ) group is not quite as robust as the SF 5 group, we find that the TeF 5 group is more stable than previously thought, thus opening a door to explore new applications of this motif., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)