Issue 8, 2021

Switching between mono and doubly reduced odd alternant hydrocarbon: designing a redox catalyst

Abstract

Since the early Hückel molecular orbital (HMO) calculations in 1950, it has been well known that the odd alternant hydrocarbon (OAH), the phenalenyl (PLY) system, can exist in three redox states: closed shell cation (12π e), mono-reduced open shell neutral radical (13π e) and doubly reduced closed shell anion (14π e). Switching from one redox state of PLY to another leads to a slight structural change owing to its low energy of disproportionation making the electron addition or removal process facile. To date, mono-reduced PLY based radicals have been extensively studied. However, the reactivity and application of doubly reduced PLY species have not been explored so far. In this work, we report the synthesis of the doubly reduced PLY species (14π e) and its application towards the development of redox catalysis via switching with the mono-reduced form (13π e) for aryl halide activation and functionalization under transition metal free conditions without any external stimuli such as heat, light or cathodic current supply.

Graphical abstract: Switching between mono and doubly reduced odd alternant hydrocarbon: designing a redox catalyst

Supplementary files

Article information

Article type
Edge Article
Submitted
30 okt 2020
Accepted
23 dec 2020
First published
23 dec 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 3039-3049

Switching between mono and doubly reduced odd alternant hydrocarbon: designing a redox catalyst

J. Ahmed, P. Datta, A. Das, S. Jomy and S. K. Mandal, Chem. Sci., 2021, 12, 3039 DOI: 10.1039/D0SC05972B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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