Biphenyl Sulfonic and Disulfonic Acids with Perfluorinated Alkyl Residues. Issue 41 (31st October 2018)

• Record Type: Journal Article
• Authors: Kahrs, Christoph; Wickleder, Mathias S.; Christoffers, Jens
• Is Part Of: European journal of organic chemistry. Issue 41(2018)
• Page Start: 5754
• Page End: 5762
• Publication Date: 2018-10-31
• Subjects: Sulfonic acids -- Fluorine compounds -- Suzuki coupling -- Heck reaction -- Boron compounds -- Palladium catalysis -- Cross coupling; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800882
• Languages: English
• ISSNs: 1434-193X

Abstract

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 1 H, 1 H, 2 H ‐perfluorinated alkenes (C6 and C8 ) 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. Abstract : Hybrid materials consisting of polar sulfonic acids, crystalline biphenyl scaffolds and amorphous fluorinated side chains are prepared by Suzuki cross coupling.