Universität zu Köln

Kremlev, Mikhail M., Mushta, Aleksej I., Tyrra, Wieland, Yagupolskii, Yurii L., Naumann, Dieter and Schaefer, Mathias ORCID: 0000-0002-5943-4335 (2015). Approaches to prepare perfluoroalkyl and pentafluorophenyl copper couples for cross-coupling reactions with organohalogen compounds. Dalton Trans., 44 (45). S. 19693 - 19700. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 1477-9234

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Abstract

The reactions of iodoperfluoroalkanes C(n)F2(n+1)I (n = 2, 3, 4) and n-BuLi at low temperatures give NMR spectroscopic evidence for LiCnF2n+1 which were converted into LiCu(CnF(2n+1))(2) derivatives upon treatment with 0.5 mol copper(I) bromide, CuBr. An alternative route to obtain perfluoroorgano copper couples, Cu(R-f)(2)Ag (R-f = n-C3F7, n-C4F9, C6F5) was achieved from the reactions of the corresponding perfluoroorgano silver(I) reagents, AgRf, and elemental copper through redox transmetallations. The composition of the resulting reactive intermediates was investigated by means of F-19 NMR spectroscopy and ESI mass spectrometry. Perfluoro-n-propyl and perfluoro-n-butyl copper-silver reagents prepared by the oxidative transmetallation route exhibited good properties in C-C bond formation reactions with acid chlorides even under moderate conditions. Substitution of bromine directly bound to aromatics for perfluoroalkyl groups was achieved at elevated temperatures, while success in halide substitution reactions using lithium copper couples remained poor.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Kremlev, Mikhail M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Mushta, Aleksej I. UNSPECIFIED UNSPECIFIED UNSPECIFIED Tyrra, Wieland UNSPECIFIED UNSPECIFIED UNSPECIFIED Yagupolskii, Yurii L. UNSPECIFIED UNSPECIFIED UNSPECIFIED Naumann, Dieter UNSPECIFIED UNSPECIFIED UNSPECIFIED Schaefer, Mathias UNSPECIFIED orcid.org/0000-0002-5943-4335 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-415556
DOI:	10.1039/c5dt02925b
Journal or Publication Title:	Dalton Trans.
Volume:	44
Number:	45
Page Range:	S. 19693 - 19700
Date:	2015
Publisher:	ROYAL SOC CHEMISTRY
Place of Publication:	CAMBRIDGE
ISSN:	1477-9234
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language SYNTHETIC CHEMISTRY; SILVER(I) FLUORIDE; ORGANIC HALIDES; ACID-CHLORIDES; TRIFLUOROMETHYLATION; COMPLEXES; IODIDES; REACTIVITY; REAGENTS; ARENES Multiple languages Chemistry, Inorganic & Nuclear Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/41555