Copper Causes Regiospecific Formation of C 4 F 8 ‐Containing Six‐Membered Rings and their Defluorination/Aromatization to C 4 F 4 ‐Containing Rings in Triphenylene/1,4‐C 4 F 8 I 2  Reactions | Zendy

Rippy Kerry C. | Zendy; Bukovsky Eric V. | Zendy; Clikeman Tyler T. | Zendy; Chen YuSheng | Zendy; Hou GaoLei | Zendy; Wang XueBin | Zendy; Popov Alexey A. | Zendy; Boltalina Olga V. | Zendy; Strauss Steven H. | Zendy

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Copper Causes Regiospecific Formation of C 4 F 8 ‐Containing Six‐Membered Rings and their Defluorination/Aromatization to C 4 F 4 ‐Containing Rings in Triphenylene/1,4‐C 4 F 8 I 2 Reactions

Author(s) -

Rippy Kerry C.,

Bukovsky Eric V.,

Clikeman Tyler T.,

Chen YuSheng,

Hou GaoLei,

Wang XueBin,

Popov Alexey A.,

Boltalina Olga V.,

Strauss Steven H.

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201504291

Subject(s) - aromatization , triphenylene , chemistry , copper , aromaticity , crystallography , ring (chemistry) , medicinal chemistry , stereochemistry , molecule , organic chemistry , catalysis

The presence of Cu in reactions of triphenylene (TRPH) and 1,4‐C 4 F 8 I 2 at 360 °C led to regiospecific substitution of TRPH ortho C(β) atoms to form C 4 F 8 ‐containing rings, completely suppressing substitution on C(α) atoms. In addition, Cu caused selective reductive‐defluorination/aromatization (RD/A) to form C 4 F 4 ‐containing aromatic rings. Without Cu, the reactions of TRPH and 1,4‐C 4 F 8 I 2 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 1 H/ 19 F NMR.

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