Issue 9, 2017

Direct amination of the antiaromatic NiII norcorrole

Abstract

We have discovered a facile amination reaction of NiII dimesitylnorcorrole, which is an antiaromatic porphyrinoid with a 16π-electron conjugation system. The amination reaction proceeded at the β-positions of the norcorrole with high regioselectivity upon treatment with various amines used as solvents. The reaction requires neither catalysts nor pre-functionalization of the norcorrole. The optical and electrochemical properties of the amino norcorroles were substantially modulated by electron-donating nitrogen atoms. According to theoretical studies, the regioselectivity of amination can be accounted for by molecular orbitals of the norcorrole.

Graphical abstract: Direct amination of the antiaromatic NiII norcorrole

Supplementary files

Article information

Article type
Research Article
Submitted
21 Apr 2017
Accepted
09 Mai 2017
First published
10 Mai 2017

Mater. Chem. Front., 2017,1, 1853-1857

Direct amination of the antiaromatic NiII norcorrole

T. Yoshida and H. Shinokubo, Mater. Chem. Front., 2017, 1, 1853 DOI: 10.1039/C7QM00176B

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