A survey of acid catalysts for use in two-step, one-flask syntheses of meso-substituted porphyrinic macrocycles.
[reaction: see text] Diverse Lewis acids and Bronsted acids were examined in the two-step, one-flask synthesis of meso-tetraphenylporphyrin, N-confused tetraphenylporphyrin, and tetraphenylsapphyrin. The scope of acid catalysis was found to be very broad, with 35 of 45 acids providing TPP in yields ranging from 5% to 58%. NC-TPP was also widely observed in yields of 1-40%, and TPS was infrequently observed in yields of <1%. Additionally, conditions were found for direct preparation of magnesium TPP and copper TPP.
Geier
G R
GR
Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA.
Ciringh
Y
Y
Li
F
F
Haynes
D M
DM
Lindsey
J S
JS
D000148:Acids, Noncarboxylic / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D011166:Porphyrins / Q000138:chemical synthesis*; D011758:Pyrroles / Q000737:chemistry
D000148:Acids, Noncarboxylic; D000447:Aldehydes; D011166:Porphyrins; D011758:Pyrroles; C409084:tetraphenylporphyrin