@article{zaidi_fico_lindsey_2006, title={Investigation of streamlined syntheses of porphyrins bearing distinct meso substituents}, volume={10}, ISSN={["1520-586X"]}, DOI={10.1021/op050193g}, abstractNote={The use of porphyrins in fundamental studies and diverse applications requires facile access to ample quantities of material in pure form. The existing conditions for the condensation of a dipyrromethane plus a dipyrromethane−dicarbinol employ 2.5 mM reactants and afford ∼30% yields with no detectable scrambling. Large-scale syntheses require condensation and oxidation conditions that function at higher concentrations. Thirty-one acids (plus additives) have been examined for reactions at 25 mM reactants using the synthesis of a trans-A2B2-porphyrin as a model. The porphyrin was formed in ∼20% yield upon condensation in CH2Cl2 at room temperature using (1) Sc(OTf)3 (3.2 mM) + 2,6-di-tert-butylpyridine (32 mM), or (2) Zn(OTf)2 (10 mM). Nine porphyrins were prepared in this manner in yields of 15−22% with no detectable scrambling, whereas three other porphyrins afforded low levels of scrambling and/or lower yields (8−14%). Conditions for the oxidation also have been investigated. The reaction of 5-mesityldip...}, number={1}, journal={ORGANIC PROCESS RESEARCH & DEVELOPMENT}, author={Zaidi, SHH and Fico, FM and Lindsey, JS}, year={2006}, pages={118–134} }