Well-Defined CuC2F5 Complexes and Pentafluoroethylation of Acid Chlorides

Four new well‐defined CuI complexes bearing a C2F5 ligand have been prepared and fully characterized: [(Ph3P)2CuC2F5] (2), [(bpy)CuC2F5] (3), [(Ph3P)Cu(phen)C2F5] (4), and [(IPr*)CuC2F5] (5). X‐ray structures of all four have been determined, showing that the C2F5‐ligated Cu atom can be di‐ (5), tri...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-04, Vol.54 (17), p.5218-5222
Main Authors: Panferova, Liubov I., Miloserdov, Fedor M., Lishchynskyi, Anton, Martínez Belmonte, Marta, Benet-Buchholz, Jordi, Grushin, Vladimir V.
Format: Article
Language:English
Subjects:
Chlorides - chemistry
Coordination Complexes - chemistry
copper
Copper - chemistry
Crystallography, X-Ray
fluorine
Fluorine - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Conformation
organometallic synthesis
pentafluoroethyl ketones
pentafluoroethylation
Phenanthrolines - chemistry
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Summary:Four new well‐defined CuI complexes bearing a C2F5 ligand have been prepared and fully characterized: [(Ph3P)2CuC2F5] (2), [(bpy)CuC2F5] (3), [(Ph3P)Cu(phen)C2F5] (4), and [(IPr*)CuC2F5] (5). X‐ray structures of all four have been determined, showing that the C2F5‐ligated Cu atom can be di‐ (5), tri‐ (2 and 3), and tetracoordinate (4). The mixed phen‐PPh3 complex 4 is a highly efficient fluoroalkylating agent for a broad variety of acid chlorides. This high‐yielding transformation represents the first general method for the synthesis of RCOC2F5 from the corresponding RCOCl. Four well‐defined CuC2F5 complexes have been prepared and fully characterized, with [(phen)Cu(PPh3)C2F5] (phen=1,10‐phenanthroline) proving to be a remarkably efficient fluoroalkylating agent for a broad variety of acid chlorides (see scheme). The procedure represents the first general method for the one‐step conversion of RCOCl into valuable pentafluoroethyl ketones.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201500341