4-(Ph3 B)-2,6-Mes2 Py]- : A Sterically Demanding Anionic Pyridine

Chemistry : a European Journal
Nadja M C SchmidlinTobias Böttcher

Abstract

The introduction of a triphenylborate group at the 4-position of 2,6-dimesitylpyridine afforded a sterically demanding anionic pyridine. The charge introduced through the borate group drastically increases its basicity and measurement of its pKa value (18.46) revealed a significantly higher value than that of 4-dimethylaminopyridine (17.95). THF ring-opening was observed upon treating its lithium salt with TMSCl, which demonstrates its high nucleophilicity. The mesityl groups at the 2,6-positions are oriented orthogonal to the pyridine ring and do not block the nitrogen atom of the pyridine. The reaction of the protonated pyridine with Li[BH4 ] yielded the corresponding Lewis acid/base adduct, which shows that the title compound can be used as a monodentate ligand in coordination chemistry. The crystal structures of all the compounds presented in this work are reported.

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Citations

Mar 27, 2020·Chemical Communications : Chem Comm·Nadja M C SchmidlinTobias Böttcher
Apr 1, 2020·The Journal of Organic Chemistry·Julian HelbergHendrik Zipse
Jan 9, 2019·Journal of the American Chemical Society·Suzanne M Jansze, Kay Severin

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