While CD3CN was the only solvent tested that worked well with electron-rich phenylboronic acids and alk(en)ylboronic acids, it failed with electron-poor phenylboronic acids. We therefore screened further solvents, and discovered that Nmethylpyrrolidone (NMP) led to clean and efficient SMC with electron-poor phenylboronic acids. 4-Fluorophenylboronic acid and phenylboronic acid could be reacted in both solvents; NMP gave higher conversion and better purity of the raw product for the fluoro compound (see Table ). Previously, NMP containing hydrochloride had been used as solvent for the introduction of a B-O bond. As the Suzuki coupling requires a base, we did not expect the formation of a B-O bond, and even traces of such a derivative were not visible in mass spectrometry. This is in contrast to the [CB9H9I] 1-cluster, which under similar conditions yields [CB9H9OH] 1-. Also, the formation of [B12H11OH] 2-, which we had observed when no other coupling partner was present, was not detected here. Thus, we have been able to establish conditions under which one can attach any carbon compound to a B atom on dodecaborate, with boronic acids that have strongly electron-withdrawing groups, as well as strongly electron-donating groups, and thereby spanning the whole spectrum of functional groups, as detailed in Table . 3-nitrophenyl B 81 [a[ Isolated yield. Boronopinacolate as substrate. [B12H11I] 2-remained after reaction overnight. The phenyl derivatives are ordered according to the size of the Hammett constants of the substituents.