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. 2017 Jun 27;82(14):7446–7462. doi: 10.1021/acs.joc.7b01128

Table 1. Yields of Porphyrin Synthesis: Influence of Concentration and Strap.

compound yield at 3.5 mMa yield at 0.35 mMa
5a 1% 6%
5b 5% 20%
5c 8% 31%
5d 0% <1%
5e 1% 6%
a

Concentration of starting material 3a–e for the porphyrin condensation. Conditions: (i) dialdehyde 3a–e (3.5 mM or 0.35 mM, 1 equiv), dipyrromethane 4 (2 equiv), TFA (2 equiv), DCM, 20 °C, 16 h; (ii) DDQ (3 equiv), 20 °C, 30 min; (iii) NEt3 (2 equiv).