A Simple and Versatile One-Pot Synthesis of meso-Substituted trans-A2B-Corroles
- 11 May 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (12) , 4267-4275
- https://doi.org/10.1021/jo010146w
Abstract
We have developed a new methodology that affords regioisomerically pure trans-A2B-corroles. The corrole formation reaction involves the acid-catalyzed condensation of a dipyrromethane and an aldehyde followed by oxidation with DDQ. Optimal conditions for the condensation were identified after examining various reaction parameters (solvent, acid, concentration, time). The conditions identified (CH2Cl2, [DPM] = 33 mM, [aldehyde] = 17 mM, [TFA] = 1.3 mM (for sterically hindered DPMs) or [TFA] = 0.26 mM (for sterically unhindered DPMs), 5 h, room temperature) resulted in the formation of corroles in 3−25% yield without detectable scrambling. The synthesis is compatible with diverse functionalities: ester, nitrile, ether, fluoro, hydroxy, iodo, nitro, thioacetate, methylsulfoxy. In total 21 corroles of type trans-A2B were prepared. Three exemplary corrole syntheses were successfully carried out at 8 mmol scale. Corroles 23, 30, and 41 (160−600 mg) were obtained in essentially the same yield as in small scale experiments.Keywords
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