Synthesis of meso-Triaryl 22-Oxanorroles

Norroles are isomers of corroles containing a direct pyrrole N–pyrrole C link instead of a pyrrole C–pyrrole C link of corroles. 22-Oxanorroles are core-modified norroles in which one of the pyrroles is replaced with a furan ring. A straightforward route is adopted to synthesize the first examples of aromatic meso-triaryl-22-oxanorroles containing a pyrrole N–pyrrole α-C direct bond in 4–7% yields by condensing 16-oxatripyrrane and (1H-pyrrol-3-yl)­(p-tolyl)­methanol in CH₂Cl₂ under mild acid-catalyzed conditions followed by oxidation with DDQ.