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A Simple and Versatile One-Pot Synthesis of meso-Substituted trans-A2B-Corroles
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.
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Cites
Spanagel, E. W., & Carothers, W. H. (1935) · Journal of the American Chemical Society · doi:10.1021/ja01308a046 · Cited by 139
Cited by
Efficient Synthesis of meso-Substituted Corroles in a H2O−MeOH Mixture
Koszarna, B., & Gryko, D. T. (2006) · The Journal of Organic Chemistry · doi:10.1021/jo060007k · Cited by 435
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Metadata
- Authors
- Gryko, D. T., & Jadach, K.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-05-11
- Volume
- 66
- Issue
- 12
- Pages
- 4267-4275
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W1999329526
- Cited by
- 173
- References
- 1
- FWCI
- 9.43
- Type
- journal article
- Language
- en
- Open access
- closed
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