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One-pot synthesis of meso-alkyl substituted isocorroles: the reaction of a triarylcorrole with Grignard reagent.

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 ?-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.

SUBMITTER: Nardis S

PROVIDER: S-EPMC3002075 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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One-pot synthesis of meso-alkyl substituted isocorroles: the reaction of a triarylcorrole with Grignard reagent.

Nardis Sara S Pomarico Giuseppe G Mandoj Federica F Fronczek Frank R FR Smith Kevin M KM Paolesse Roberto R

Journal of porphyrins and phthalocyanines 20100801 8

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 ...[more]

PMID: 21165169

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