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Synthesis of Meso-Diarylaminocorroles via S_NAr Reactions.

ABSTRACT: A corrole is a tetrapyrrolic macrocycle known as a ring-contracted porphyrinoid. Despite the progress of the synthetic chemistry of meso-aryl-substituted corroles since the early 2000s, meso-heteroatom-substituted corroles have been scarcely reported. Herein we report that the S_NAr-type substitution reaction of a meso-chlorocorrole silver complex with diphenylamine or carbazole in the presence of NaH as a base produced meso-aminocorroles. The structures, ultraviolet?visible spectroscopy (UV/Vis), and emission spectra of these meso-aminocorroles were discussed. Furthermore, the oxidation reaction of a meso-diphenylaminocorrole was examined, which resulted in the formation of 10,10-diethoxyisocorrole.

SUBMITTER: Ueta K

PROVIDER: S-EPMC6384549 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Synthesis of Meso-Diarylaminocorroles via SNAr Reactions.

Ueta Kento K Tanaka Takayuki T Osuka Atsuhiro A

Molecules (Basel, Switzerland) 20190212 3

A corrole is a tetrapyrrolic macrocycle known as a ring-contracted porphyrinoid. Despite the progress of the synthetic chemistry of meso-aryl-substituted corroles since the early 2000s, meso-heteroatom-substituted corroles have been scarcely reported. Herein we report that the SNAr-type substitution reaction of a meso-chlorocorrole silver complex with diphenylamine or carbazole in the presence of NaH as a base produced meso-aminocorroles. The structures, ul ...[more]

PMID: 30759763

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