Journal
INORGANICS
Volume 11, Issue 5, Pages -Publisher
MDPI
DOI: 10.3390/inorganics11050188
Keywords
Stille reaction; stannylation; copper(I)-thiophene-2-carboxylate; 4-(pyrazin-2-yl)-1; 3-dithiol-2-one ligand systems; acetalization
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Several synthetic cross-coupling procedures were evaluated for tethering pyrazine to dithiocarbonates. The resulting compounds can serve as pro-ligands and can be converted into ene-dithiolate ligand systems resembling molybdopterin by removing the C=O moiety. The coupling of 2-iodopyrazine with stannylated dithiocarbonate units mediated by copper(I)-thiophene-2-carboxylate in stoichiometric equivalents proved to be the most efficient and reliable method for synthesizing the targeted compounds.
Several synthetic cross-coupling procedures were (re-)evaluated for the tethering of pyrazine to dithiocarbonates. The resultant species constitute pro-ligands and can be converted by removal of the C=O moiety into ene-dithiolate ligand systems that model molybdopterin. The coupling of 2-iodopyrazine with the stannylated dithiocarbonate units mediated by copper(I)-thiophene-2-carboxylate in stoichiometric equivalents proved to be the most efficient and the only reliable route to the targeted compounds. Single-crystal X-ray structural analysis confirmed the final structures of two pursued pyrazine-derived dithiocarbonates and those of two intermediates.
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