Synthesis of a B12–BODIPY dyad for B12-inspired photochemical transformations of a trichloromethylated organic compound

Yuki Anai; Keita Shichijo; Mamoru Fujitsuka; Yoshio Hisaeda; Hisashi Shimakoshi

doi:10.1039/D0CC04274A

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Synthesis of a B₁₂–BODIPY dyad for B₁₂-inspired photochemical transformations of a trichloromethylated organic compound†

Yuki Anai,^a Keita Shichijo,^a Mamoru Fujitsuka,

^b Yoshio Hisaeda

*^a and Hisashi Shimakoshi

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Nishi-ku, Motooka, Fukuoka 744, 819-0395, Japan
E-mail: yhisatcm@mail.cstm.kyushu-u.ac.jp, shimakoshi@mail.cstm.kyushu-u.ac.jp

^b The Institute of Scientific and Industrial Research (SANKEN), Osaka University, Osaka, 567-0047, Japan

Abstract

A B₁₂ complex–BODIPY dyad was synthesized by peripheral modification of cobalamin derivatives. The photophysical properties of the dyad were investigated by UV-vis, PL, and transient absorption spectroscopy. A visible light-driven dechlorination reaction of a trichlorinated organic compound, DDT, was reported. The dyad showed efficient catalysis for dechlorination under N₂ with turnover numbers of over 220 for the reaction. One-pot syntheses of an ester and amide from DDT and benzotrichloride were also achieved using the dyad under air.

This article is part of the themed collection: Bioinspired metal complexes for chemical transformations and catalysis

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DOI: https://doi.org/10.1039/D0CC04274A
Article type: Communication
Submitted: 19 jun. 2020
Accepted: 04 sep. 2020
First published: 05 sep. 2020

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Chem. Commun., 2020,56, 11945-11948

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Synthesis of a B₁₂–BODIPY dyad for B₁₂-inspired photochemical transformations of a trichloromethylated organic compound

Y. Anai, K. Shichijo, M. Fujitsuka, Y. Hisaeda and H. Shimakoshi, Chem. Commun., 2020, 56, 11945 DOI: 10.1039/D0CC04274A

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Chemical Communications