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Serendipitous formation of meso-free corroles in the [3+1] porphyrin and [3+2] sapphyrin syntheses

Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan

E-mail Address: uno@ehime-u.ac.jp

Correspondence to: Hidemitsu Uno, Tel: +81-89-927-9610, Fax: +81-89-927-9612.

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Shota Konishi

Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan

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Jun Nakamura

Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan

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Shigeki Mori

Advanced Research Support Center, Ehime University, Matsuyama 790-8577, Japan

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Masayoshi Takase

Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan

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Tetsuo Okujima

Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan

E-mail Address: okujima.tetsuo.mu@ehime-u.ac.jp

Correspondence to: Tetsuo Okujima, Tel: +81-89-927-9615, Fax: +81-89-927-9612.

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https://doi.org/10.1142/S1088424622500900Cited by:0 (Source: Crossref)

Abstract

During the preparative investigation of $π$ -expanded porphyrinoids based on the retro-Diels-Alder reaction of bicyclo[2.2.2]octadiene(BCOD)-fused precursors for benzo- and benzo[ $k$ ]fluorantho[9,10]-[ $b$ ]porphyrins by the [3+1] porphyrin synthesis using tripyrrane-1,14-dicarbaldehyde and BCOD-fused pyrroles, serendipitous formation of the corresponding corroles was observed. After elucidation of the reaction conditions, the [3+1] reaction afforded 21,31-dihydro-21,31-ethanobenzo[ $k$ ]fluorantho[9,10- $b$ ]corrole in 23% yield as well as a trace amount of the corresponding porphyrin. In the sapphyrin synthesis by the [3+2] approach using the tripyrrane-1,14-dicarbaldehyde and a bipyrrole, the similar reaction conditions resulted in the formation of 5-pyrrolylcorrole in a 38% yield as well as isosmaragdyrin and the originally targeted sapphyrin.

Dedicated to Prof. Tomás Torres on the occasion of his 70^th birthday

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