Carbon-substituted 9,12-dimercapto-1,2-dicarba-closo-dodecaboranes via a 9,12-bis(methoxy-methylthio)-1,2-dicarba-closo-dodecaborane precursor

Dithiolated derivatives of 1,2-dicarba-closo-dodecaboranes are common ligands to be used for self-assembling monolayers, nanoparticles or transition complexes due to their robust molecular structure. The 9,12-dimercapto-1,2-dicarba-closo-dodecaborane, a derivative with two SH-groups in adjacent positions, is an interesting unit for the preparation of derivatives additionally functionalized in positions one and two. In this contribution, we report a convenient synthesis of 1,2-disubstituted 9,12-dimercapto-1,2-dicarba-closo-dodecaboranes starting from the 9,12-dimercapto-1,2-dicarba-closo-dodecaboranes with SH groups protected using methoxy-methyl (MOM) groups. All compounds are well characterized via HiRes-mass spectroscopy, 1H, 13C and 11B NMR-spectroscopy and IR spectroscopy. The precursor 9,12-bis(methoxy-methylthio)-1,2-dicarba-closo-dodecaborane was additionally characterized with X-ray-structural analysis.

9,12-Dimercapto-1,2-disubstituted-o-carborane derivatives can be conveniently synthesized via a novel 9,12-bis(methoxy-methylthio)-o-carborane precursor. After introducing substituents at positions 1 and 2 and removing the protecting methoxy-methyl groups the thiol functionalities are available for further modifications.Figure optionsDownload as PowerPoint slide