Copper Causes Regiospecific Formation of C4F8‐Containing Six‐Membered Rings and their Defluorination/Aromatization to C4F4‐Containing Rings in Triphenylene/1,4‐C4F8I2 Reactions |
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| Authors: | Kerry C Rippy Dr Eric V Bukovsky Dr Tyler T Clikeman Dr Yu‐Sheng Chen Dr Gao‐Lei Hou Dr Xue‐Bin Wang Dr Alexey A Popov Dr Olga V Boltalina Prof Steven H Strauss |
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| Affiliation: | 1. Department of Chemistry, Colorado State University, Fort Collins, CO, USA;2. ChemMatCARS, University of Chicago Advanced Proton Source, Argonne, IL, USA;3. Physical Sciences Division, Pacific Northwest National Laboratory, Richland, WA, USA;4. Leibniz Institute for Solid State and Materials Research, Dresden, Germany |
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| Abstract: | The presence of Cu in reactions of triphenylene (TRPH) and 1,4‐C4F8I2 at 360 °C led to regiospecific substitution of TRPH ortho C(β) atoms to form C4F8‐containing rings, completely suppressing substitution on C(α) atoms. In addition, Cu caused selective reductive‐defluorination/aromatization (RD/A) to form C4F4‐containing aromatic rings. Without Cu, the reactions of TRPH and 1,4‐C4F8I2 were not regiospecific and no RD/A was observed. These results, supported by DFT calculations, are the first examples of Cu‐promoted 1) regiospecific perfluoroannulation, 2) preparative C?F activation, and 3) RD/A. HPLC‐purified products were characterized by X‐ray diffraction, low‐temperature PES, and 1H/19F NMR. |
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| Keywords: | aromatization copper perfluoroalkylation triphenylene X-ray structure |
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