Two-Step, One-Flask
Synthesis of a Meso-Substituted
Phlorin
Version 4 2017-05-27, 13:13
Version 3 2016-06-13, 13:26
Version 2 2016-05-31, 21:43
Version 1 2016-05-27, 15:21
Posted on 2017-05-27 - 13:13
A two-step,
one-flask reaction of pyrrole with pentafluorobenzaldehyde
and acetone was investigated to determine the potential for a streamlined
synthesis of a phlorin and/or 5-isocorrole as an alternative to stepwise,
dipyrromethanecarbinol routes. Analytical-scale reactions were performed
examining the effect of reactant concentration, reactant ratio, acid
catalyst (TFA or BF3·OEt2), concentration
of acid catalyst, oxidant quantity, and reaction time on the distribution
of phlorin and 5-isocorrole as well as three additional porphyrinoids
(porphodimethene, porphyrin, and corrole). Phlorin was observed ubiquitously
in yields up to 20–26%, whereas 5-isocorrole was not detected.
Promising reaction conditions for the one-flask synthesis of the phlorin
were performed on a preparative scale. The best reaction condition
afforded the phlorin in an isolated yield of 20–21% (249–268
mg). Preliminary attempts to extend the methodology to the preparation
of phlorins derived from other ketones resulted in a low yield of
phlorin from acetophenone (5%) and no detectable phlorin from benzophenone.
The discovery of reaction conditions for the two-step, one-flask synthesis
of a phlorin provides easier access to this interesting compound,
and provides encouragement for the further study of reactions of pyrrole
with an aldehyde and a ketone.
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Kim, Dongjoon; Chun, Hao-Jung; Donnelly, Christopher C.; Geier, G. Richard (2016). Two-Step, One-Flask
Synthesis of a Meso-Substituted
Phlorin. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.6b00571
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AUTHORS (4)
DK
Dongjoon Kim
HC
Hao-Jung Chun
CD
Christopher C. Donnelly
GG
G. Richard Geier