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The reaction of dipyrromethanedicarbinols with pyrrole leading to meso-substituted corroles was investigated to determine whether mild acid catalysts [Dy(OTf)₃, Yb(OTf)₃, Sc(OTf)₃, and InCl₃] known to provide porphyrins from dipyrromethanecarbinol species while suppressing undesired reversibility (resulting in scrambling) are applicable to reactions affording corrole, and to explore the requirements of the oxidation step. We examined a model reaction leading to meso-triphenylcorrole (TPC) to survey the effect of acid catalyst, acid concentration, ratio of pyrrole to dipyrromethanedicarbinol, oxidant, oxidant quantity, and reaction time on the yield of TPC (by UV−vis) in reactions performed at room temperature in CH₂Cl₂. Key to this survey was a modification of the well-known spectrophotometric method for monitoring reactions leading to porphyrin. The survey revealed that TPC could be prepared via a subset of the …