Tetraphenyloxybenziporphyrin, a new organometallic ligand for silver(III) and gold(III)

Org Lett. 2006 Nov 9;8(23):5263-6. doi: 10.1021/ol062108a.


[Structure: see text] Reaction of 4-hydroxyisophthalaldehyde with excess phenyl magnesium bromide gave a dicarbinol and this condensed with pyrrole and aromatic aldehydes in the presence of BF3.Et2O to afford, following oxidation with DDQ, novel tetraarylcarbaporphyrinoids in 10-24% yield. Further reaction with silver(I) acetate or gold(III) acetate gave stable organometallic derivatives that retained the aromatic characteristics of the parent macrocycle.