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C31-Selective substitution of cationic N-heteroaromatic groups into a 3-vinylated chlorophyll-a derivative

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Abstract

A variety of N-containing heteroarenes were site-selectively introduced at the C31-position of a chlorophyll-a derivative possessing a 3-vinyl group through a C–N+ bond via oxidative reactions using iodine in the presence of a silver(I) salt. Electron-rich N-heteroarenes were effectively substituted, while electron-withdrawing or bulky nitrogen-neighboring substituents suppressed the reactivities. The cationic products formed were characterized by 1D/2D NMR, and their optical properties were also investigated.

Graphical abstract: C31-Selective substitution of cationic N-heteroaromatic groups into a 3-vinylated chlorophyll-a derivative

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Publication details

The article was received on 17 Jan 2019, accepted on 05 Mar 2019 and first published on 06 Mar 2019


Article type: Communication
DOI: 10.1039/C9OB00130A
Citation: Org. Biomol. Chem., 2019, Advance Article

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    C31-Selective substitution of cationic N-heteroaromatic groups into a 3-vinylated chlorophyll-a derivative

    T. Takahashi, S. Ogasawara, S. Echizen, Y. Shinozaki and H. Tamiaki, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00130A

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