Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 42, Pages 12898-12902Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706237
Keywords
fluorine; high-valent species; nickel; reaction mechanisms; trifluoromethylation
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Funding
- ANR program [ANR-12-BS07-001601]
- CNRS
- Universite de Toulouse
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The robust, high-valent Ni-IV complex [(Py)(2)(NiF2)-F-IV(CF3)(2)] (Py=pyridine) was synthesized and fully characterized by NMR spectroscopy, X-ray diffraction, and elemental analysis. It reacts with aromatic compounds at 25 degrees C to form the corresponding benzotrifluorides in nearly quantitative yield. The monomeric and dimeric (NiCF3)-C-III complexes 2Py and 2 were identified as key intermediates, and their structures were unambiguously determined by EPR spectroscopy and X-ray diffraction. Preliminary kinetic studies in combination with the isolation of reaction intermediates confirmed that the C-H bond-breaking/C-CF3 bond-forming sequence can occur both at (NiCF3)-C-IV and (NiCF3)-C-III centers.
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