Biphenyl Sulfonic and Disulfonic Acids with Perfluorinated Alkyl Residues
Biphenyl Sulfonic and Disulfonic Acids with Perfluorinated Alkyl Residues
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DOI：
10.1002/ejoc.201800882
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发表时间：
2018-10
影响因子：
2.8
通讯作者：
Christoph Kahrs;M. Wickleder;J. Christoffers
中科院分区：
文献类型：
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作者：
Christoph Kahrs;M. Wickleder;J. Christoffers
磺酸是配位聚合物中羧酸的有趣但尚未深入研究的替代品。在这项研究中，我们提出了与极性，刚性联苯部分和无序的高度氟化的烷基链的杂化磺酸的合成。因此，制备了八种具有一个或两个全氟烷基链的联苯磺酸和二磺酸。合成中的关键步骤包括两个钯催化的C-C键形成：全氟烷基残基通过使用1H，1H，2 H-全氟烯烃（C6和C8）的Heck反应（高达91%）安装，联苯单元通过带有一个或两个受保护硫醇基团的硼酸的Suzuki偶联（高达88%）建立。最后，通过N-氯代琥珀酰亚胺介导的氧化，然后水解相应的磺酰氯，将这些硫醇基团转化为磺酸。
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 (C6and 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 byN‐chlorosuccinimide mediated oxidation followed by hydrolysis of the respective sulfonyl chloride.