Kahrs, Christoph, Wickleder, Mathias S. and Christoffers, Jens (2018). Biphenyl Sulfonic and Disulfonic Acids with Perfluorinated Alkyl Residues. Eur. J. Org. Chem., 2018 (41). S. 5754 - 5763. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

Sulfonic acids serve as interesting, yet not intensively studied alternatives to carboxylic acids as linker units in coordination polymers. In this study, we present the synthesis of hybrid sulfonic acids with polar, rigid biphenyl moieties and disordered highly fluorinated alkyl chains. Consequently, eight biphenyl sulfonic and disulfonic acids with one or two perfluoroalkyl chains were prepared. The key steps within the synthesis include two palladium catalyzed C-C bond formations: The perfluoroalkyl residue is installed by Heck reaction (up to 91 %) using 1H,1H,2H-perfluorinated alkenes (C-6 and C-8) and the biphenyl unit is established by a Suzuki coupling (up to 88 %) of boronic acids bearing one or two protected thiol groups. Finally, these thiol groups are converted into the sulfonic acids by N-chlorosuccinimide mediated oxidation followed by hydrolysis of the respective sulfonyl chloride.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Kahrs, ChristophUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Wickleder, Mathias S.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Christoffers, JensUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-165904
DOI: 10.1002/ejoc.201800882
Journal or Publication Title: Eur. J. Org. Chem.
Volume: 2018
Number: 41
Page Range: S. 5754 - 5763
Date: 2018
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1099-0690
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
METAL-ORGANIC FRAMEWORKS; CHEMISTRY; MEMBRANES; SYSTEMS; DESIGN; LINKER; PFOSMultiple languages
Chemistry, OrganicMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/16590

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