Multidentate ligands involving tethered pyridyl groups coordinated to transition metal ions have been frequently used to mimic many motifs of histidine and carboxylate endogenous ligating residues found in bioinorganic metalloenzymes. It is of interest to immobilize these ligand chelates onto heterogeneous supports. This, however, requires the use of bromine-substituted (chloromethyl)pyridines, whose current synthetic routes involve the use of extremely pyrophoric chemicals, such as n-butyllithium that require cryogenic reaction conditions, and toxic chemicals, such as thionyl chloride, that are challenging to handle and require extensive hazard controls. Herein, we discuss our recent efforts to improve on these synthetic routes through the use of grignard reagents and other chlorinating agents that are easier to handle, form less toxic byproducts, and require milder reaction conditions. The extensive characterization of these bromine-substituted pyridine precursors through the use of <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, and FT-IR spectroscopies and gas chromatography electron ionization mass spectrometry (EI GC-MS) will also be discussed.

Facile synthesis and characterization of a bromine-substituted (chlormethyl)pyridine precursor towards the immobilization of biomimetic metal ion chelates on functionalized carbons

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ACS Fall 2022

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