Method of making porphyrins
A method of making a compound of Formula I: is carried out by condensing a pair of compounds of Formula II (which pair may be the same or different), or by condensing a compound of Formula III with a compound Formula IV, to produce a compound of Formula I. The condensing step may be carried out with a metal salt under basic conditions.
1. A method of making porphine, comprising:
condensing (a) (i) 1-formyl dipyrromethane with itself, (ii), condensing 1,9-diformyldipyrromethane with dipyrromethane, or (iii) concurrently both condensing 1-formyl dipyrromethane with itself while also condensing 1,9-diformyldipyrromethane with dipyrromethane, with (b) a metal salt under basic conditions to produce said porphine;
wherein said metal salt is a magnesium, zinc, nickel or indium salt.
2. The method of claim 1 , wherein said condensing comprises condensing 1-formyl dipyrromethane with itself.
3. The method of claim 1 , wherein said condensing comprises condensing 1,9-diformyldipyrromethane with dipyrromethane.
4. The method of claim 1 , wherein said condensing comprises concurrently condensing 1-formyl dipyrromethane with itself while also condensing 1,9-diformyldipyrromethane with dipyrromethane.
5. The method of claim 1 , wherein said metal salt is a magnesium or zinc salt.
6. The method of claim 1 , wherein said metal salt is a magnesium halide.
7. The method of claim 1 , further comprising the step of displacing said metal to form free base porphine.
8. The method of claim 1 , wherein said self-condensing step is carried out by microwave irradiation.
9. The method of claim 1 , wherein said self-condensing step is carried out in a non-coordinating or weakly coordinating solvent.
10. The method of claim 1 , wherein said self-condensing step is carried out in a non-coordinating or weakly coordinating solvent in the presence of a non-coordinating or weakly coordinating base.