Functionalization of 2,3-disubstituted-2,3-dihydro-5,10,15,20- tetraphenylporphyrins
A reduced pyrrole subunit directs electrophilic functionalizations of dihydroporphyrins to the antipodal pyrrole ring by confining the chromophore 18-π-electron delocalization pathway to its N(22)H-N(24)H tautomer. The 2,3- disubstituents inhibit oxidation, this being exemplified by the synthesis of perbrominated dodecasubstituted metallochlorins. Regiospecific nitration (using N2O4) of metal-free chlorins provides access to Michael acceptors such as 12-nitro-2,3-disubstituted chlorins which are used in the preparation of highly functionalized tetraaryl-bacteriochlorins by conjugate addition of carbon-centered nucleophiles. (C) 2000 Elsevier Science Ltd.
Publication Source (Journal or Book title)
Shea, K., Jaquinod, L., Khoury, R., & Smith, K. (2000). Functionalization of 2,3-disubstituted-2,3-dihydro-5,10,15,20- tetraphenylporphyrins. Tetrahedron, 56 (20), 3139-3144. https://doi.org/10.1016/S0040-4020(00)00233-7