ArticleJournal of porphyrins and phthalocyanines2010
One-pot synthesis of meso-alkyl substituted isocorroles: the reaction of a triarylcorrole with Grignard reagent.
Article in Journal of porphyrins and phthalocyanines, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- The Hyperporphyrin Concept: A Contemporary Perspective.JACS Au · 2022Review
- Nucleophilic Aromatic Substitution (SEuropean journal of organic chemistry · 2021Review
- The Selective Monobromination of a Highly Sterically Encumbered Corrole: Structural and Spectroscopic Properties of Fe(Cl)(2-Bromo-5,10,15-tris(triphenyl)phenyl corrole).Journal of porphyrins and phthalocyanines · 2021Article
- A Leopard Cannot Change Its Spots: Unexpected Products from the Vilsmeier Reaction on 5,10,15-Tritolylcorrole.Molecules (Basel, Switzerland) · 2020Article
- β-Octabromo- and β-Octakis(trifluoromethyl)isocorroles: New Sterically Constrained Macrocyclic Ligands.ChemistryOpen · 2017Article
- Phenyl derivative of iron 5,10,15-tritolylcorrole.Inorganic chemistry · 2014Article
- β-Nitro-5,10,15-tritolylcorroles.Inorganic chemistry · 2012Article
- Amination reaction on copper and germanium β-nitrocorrolates.Inorganic chemistry · 2011Article
- Functionalization of the corrole ring: the role of isocorrole intermediates.Chemical communications (Cambridge, England) · 2011Article
- One-pot synthesis of meso-alkyl substituted isocorroles: the reaction of a triarylcorrole with Grignard reagent.Journal of porphyrins and phthalocyanines · 2010Article
- Demetalation of silver(III) corrolates.Inorganic chemistry · 2009Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
The reaction of 5,10,15-tritolylcorrole with EtMgBr opens the way for novel functionalizations of the corrole ring. DDQ oxidation of the macrocycle, followed by addition of the Grignard reagent, led to the formation of 5- and 10-alkyl substituted isocorroles in satisfying yields. Together with the one-pot formation of these isocorrole isomers, the use of such a nucleophile evidenced the competitive reactivity of the macrocycle β-positions, leading to the formation of 2-bromo- and 3-bromo-5,10,15-tritolylcorrole. While the formation of these monobromocorrole derivatives is not unprecedented, this is the first time the isomers have been separated and fully characterized. Furthermore, the higher yields of the 2-substituted species highlight a useful regioselectivity for the substitution reaction.
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Registered trials
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