An efficient one-flask synthesis of N-confused tetraphenylporphyrin.
[formula: see text] N-Confused meso-substituted porphyrin is a porphyrin isomer previously available from one-flask porphyrin syntheses as a low-yield byproduct (< 7.5%). We have found that methanesulfonic acid catalyzed condensation of pyrrole and benzaldehyde followed by DDQ oxidation provides N-confused tetraphenylporphyrin (NC-TPP) in up to 39% yield in analytical scale experiments. Preparative synthesis provided an isolated yield of 35% (800 mg). This represents a > 5-fold yield improvement and makes significant quantities of NC-TPP readily available.
Geier
G R
GR
Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA.
Haynes
D M
DM
Lindsey
J S
JS
D002851:Chromatography, High Pressure Liquid; D011166:Porphyrins / Q000138:chemical synthesis*
D011166:Porphyrins; C409084:tetraphenylporphyrin