A survey of acid catalysts for use in two-step, one-flask syntheses of meso-substituted porphyrinic macrocycles

Organic Letters

Volumn 2, Issue 12, 2000, Pages 1745-1748

  Geier III, G Richard ^a   Ciringh, Yangzhen ^a   Li, Feirong ^a   Haynes, Denise M ^a   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; INORGANIC ACID; PORPHYRIN; PYRROLE DERIVATIVE; TETRAPHENYLPORPHYRIN;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ACIDS, NONCARBOXYLIC; ALDEHYDES; CATALYSIS; PORPHYRINS; PYRROLES;

EID: 0034658882     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005917h     Document Type: Article

References (26)

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2. Lindsey, J. S. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 1, pp 45-118.
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12. The preliminary acid screening experiments also allowed identification of acids providing high yields of other porphyrinic products. At appropriate concentration, methanesulfonic acid and p-toluenesulfonic acid gave rise to a strong peak at 438 nm (characteristic of the NC-TPP Soret band) in the UV-vis spectrum of the crude, oxidized reaction mixture (see Supporting Information). Thus, prior to more detailed experiments, it was clear that those acids were good catalysts for NC-TPP formation. No other acids provided clear evidence for NC-TPP, and no acids showed peaks associated with tetraphenylsapphyrin (TPS) in these screening experiments.
13. 4c Furthermore, the Soret band of TPC is almost identical to that of TPP, making UV-vis detection of small quantities impossible. LD-MS analysis of crude reaction mixtures provided our only means to qualitatively address TPC formation. No peak or a minor peak at m/z = 526 (mass of TPC) was observed, indicating that TPC is probably a minor product or absent under the conditions found to be optimal for TPP formation for each acid.
14. The analytically determined yields of TPP, NC-TPP, and TPS reported here compare well with isolated yields in all cases where preparative scale synthesis has been performed.
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