Control of Oligomerization and Oxidation Steps in the Synthesis of Tris(pentafluorophenyl)corrole.
- Resource Type
- Article
- Authors
- Blumenfeld, Carl; Fisher, Katherine J.; Henling, Lawrence M.; Grubbs, Robert H.; Gray, Harry B.; Virgil, Scott C.
- Source
- European Journal of Organic Chemistry. May2015, Vol. 2015 Issue 14, p3022-3025. 4p.
- Subject
- *OLIGOMERIZATION
*RING formation (Chemistry)
*AROMATIC compounds
*INTERMEDIATES (Chemistry)
*HIGH performance liquid chromatography
*NUCLEAR magnetic resonance spectroscopy
*MASS spectrometry
*PYRROLES
- Language
- ISSN
- 1434-193X
The mechanistic features of oligomerization and oxidative cyclization steps in the synthesis of tris(pentafluorophenyl)corrole ( 1) have been thoroughly studied. Separation of the intermediates by preparative HPLC and analysis by NMR spectroscopy and high resolution mass spectrometry allowed for the identification of product-forming intermediates and monitoring of undesired byproducts. Conditions for complete end-capping with pyrrole were optimized for improved yields of oligomers leading to the desired corrole 1. A yield of 84 % was achieved during oxidation of an isolated precursor; the overall yield of 1 was 17.0 %. [ABSTRACT FROM AUTHOR]