Copper Causes Regiospecific Formation of C4F8-Containing Six-Membered Rings and their Defluorination/Aromatization to C4F4-Containing Rings in Triphenylene/1,4-C4F8I2 Reactions

被引：13

作者：

Rippy, Kerry C. ^{[1
]}

Bukovsky, Eric V. ^{[1
]}

Clikeman, Tyler T. ^{[1
]}

Chen, Yu-Sheng ^{[2
]}

Hou, Gao-Lei ^{[3
]}

Wang, Xue-Bin ^{[3
]}

Popov, Alexey A. ^{[4
]}

Boltalina, Olga V. ^{[1
]}

Strauss, Steven H. ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

[2] Univ Chicago Adv Proton Source, ChemMatCARS, Argonne, IL 60439 USA

[3] Pacific NW Natl Lab, Div Phys Sci, Richland, WA 99352 USA

[4] Leibniz Inst Solid State & Mat Res, D-01069 Dresden, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 03期

基金：

美国国家科学基金会;

关键词：

aromatization; copper; perfluoroalkylation; triphenylene; X-ray structure; F BOND ACTIVATION; ARENE-PERFLUOROARENE INTERACTIONS; ORGANIC SEMICONDUCTORS; RADICAL PERFLUOROALKYLATION; RATE CONSTANTS; FLUOROALKYLATION; CORANNULENE; CYCLIZATION; AROMATICS; REAGENTS;

D O I：

10.1002/chem.201504291

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The presence of Cu in reactions of triphenylene (TRPH) and 1,4-C4F8I2 at 360 degrees C led to regiospecific substitution of TRPH ortho C(beta) atoms to form C4F8-containing rings, completely suppressing substitution on C(alpha) 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 H-1/F-19 NMR.

引用

页码：874 / 877

页数：4

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