text: Hydrolysis is one of the primary reactions to occur in diboryl porphyrin complexes. In this reaction, RBOBR(por) reacts with water to exchange a B-OH bond for a B-R bond, liberating the R group.
  Hydrolysis products are important intermediates in the synthesis of the B-O-B(por) compounds from BX(por) compounds. In fact, simply performing column chromatography on (BF)(por) on silica gives the partial hydrolysis product BOF(por).
  DFT computations show that hydrolysis, as in the scheme shown here, is energetically favorable (breaking of a relatively weak B-C bond, formation of a strong B-O bond, formation of benzene). However, only one of the two phenyl groups is observed to undergo hydrolysis. This suggests thermodynamic favorability is not the only factor at play. Rather, as Belcher et al. suggest, there is a significant steric component to this reaction. The boron in the porphyrin ring plane undergoes substitution, while the out-of-plane boron retains its phenyl bond.