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Pyridine and Pyrimidine Functionalized Benzene Sulfonic and Disulfonic Acids as New Linker Compounds for Coordination Polymers
Author(s) -
Kahrs Christoph,
Schmidtmann Marc,
Wickleder Mathias S.,
Christoffers Jens
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801184
Subject(s) - chemistry , sulfonic acid , linker , pyrimidine , pyridine , sonogashira coupling , polymer chemistry , residue (chemistry) , organic chemistry , combinatorial chemistry , catalysis , palladium , stereochemistry , computer science , operating system
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 pyridine and pyrimidine units as additional nitrogen donor moieties. Four biaryl compounds consisting of a 4‐mono‐ or 3,5‐disulfophenyl ring and a 4‐pyridyl or 5‐pyrimidyl residue were prepared by Suzuki coupling reaction. In these cases, tert ‐butylthio groups were utilized as precursor functions for the sulfonic acid residues. The tert ‐butyl residues were cleaved with BBr 3 , the intermediate thiols trapped with acetyl chloride and then oxidized with H 2 O 2 . Furthermore, two pyrimidine derivatives with 5‐ethynyl linkers and 4‐mono‐ and 3,5‐disulfophenyl moieties were prepared by Sonogashira coupling. In these cases, the sulfonic acids were applied as neopentyl esters. Finally, the neopentyl groups were simply cleaved by thermolysis.