Boron complexation strategy for use in manipulating 1-acyldipyrromethanes
A method of making a metal complex comprises combining a 1-monoacyldipyrromethane with a compound of the formula R 1 R 2 MX, wherein M is boron, R 1 and R 2 are each independently organic substituents; and X is an anion leaving group; to produce a metal complex of the formula DMR 1 R 2 wherein DH is a 1-monoacyldipyrromethane. The methods and complexes are useful for the purification and synthesis of dipyrromethanes and porphyrins.
1. A method of making a porphyrin, comprising:
providing a 1-monoacyldipyrromethane-boron complex of the formula DMR 1 R 2 , wherein:
D is a 1-monoacyldipyrromethane,
M is boron, and
R 1 and R 2 are each independently selected from the group consisting of alkyl, alkenyl, alkynyl, and aryl, each of which can be unsubstituted or substituted one or more times with a substituent selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, alkoxy, alkylcarbonyl, alkylcarbonyloxy, alkylsulfinyl, alkylsulfonyl, alkylthio, halo, cyano, nitro, sulfo, oxo, formyl, azido, and carbamoyl; and then
reducing said 1-monoacyldipyrromethane in said complex without prior decomplexation of said boron to produce said porphyrin.
2. The method of claim 1 , wherein said reducing step is carried out with NaBH 4 in an organic solvent.