I have been trying to attach the pictured mesityl-sulfane ligand to 9,10-dibromo, 9,10 - diboroanthracene (DBA). I have tried the three rxn approaches listed (lithiation with tbuLi, grignard, TMS conversion). There is precedent for any one of these reactions being used to attach ligands to DBA, but not specifically a mes sulfane ligand.
None of these reactions thus far have delivered good results. The lithiation seems to give some amount of product based on NMR and mass spec, but the reaction yield is very messy and not feasible to purify. The TMS mes sulfane doesn't react with DBA at all under the given conditions. The grignard of the mes sulfane is difficult to generate reliably, it seemed to form fine when I tested the reaction with BF(mes)2, but did not genreate at all when reacted with DBA (just got starting materials back).
Does anyone have any input on why this ligand will not bond to DBA?
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