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Regioselective Aromatic Borylation in an Inert Solvent

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journal contribution
posted on 08.08.2001, 00:00 by Man Kin Tse, Jian-Yang Cho, Milton R. Smith
A protocol for performing Rh catalyzed aromatic borylations in cyclohexane has been devised. Borylation at the 5-position of several 1,3-substituted aromatic species ranging from electron-rich (1,3-(NMe2)2C6H4) to electron-deficient (1,3-(CF3)2C6H4) yields the corresponding aryl boronate esters. Veratrole was selectively borylated at the 4-position, thus extending regioselectivity to 1,2-substituted benzenes. Selective borylation at the 3-position of an N-protected pyrrole has also been demonstrated, providing a valuable reagent for cross-coupling reactions in a single step.