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Issue 14, 2019
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Direct access to 2-aryl substituted pyrrolinium salts for carbon centre based radicals without pyrrolidine-2-ylidene alias cyclic(alkyl)(amino)carbene (CAAC) as a precursor

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Abstract

The synthesis of organic radicals is challenging due to their inherent instability. In recent years, cyclic(alkyl)(amino)carbene (CAAC)-derived 2-substituted pyrrolinium salts have been used as synthons for the synthesis of isolable carbon-based radicals. Herein, we report a direct, easy and convenient method for the synthesis of 2-aryl substituted pyrrolinium salts without using CAAC as a precursor. These cations can be reduced to the corresponding radicals. The influence of the aryl substituent at the C-2 position on radical stabilization and dimerization has been investigated. Because of the large scope of our strategy (capability to modulate different substituents at all the C- and N-centres of the pyrrolinium salts), it has the merit to be an extremely effective and productive route for generating carbon-based radicals whose stability as well as reactivity can be varied.

Graphical abstract: Direct access to 2-aryl substituted pyrrolinium salts for carbon centre based radicals without pyrrolidine-2-ylidene alias cyclic(alkyl)(amino)carbene (CAAC) as a precursor

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Supplementary files

Article information


Submitted
07 Dec 2018
Accepted
27 Feb 2019
First published
28 Feb 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 4077-4081
Article type
Edge Article

Direct access to 2-aryl substituted pyrrolinium salts for carbon centre based radicals without pyrrolidine-2-ylidene alias cyclic(alkyl)(amino)carbene (CAAC) as a precursor

D. Mandal, S. Sobottka, R. Dolai, A. Maiti, D. Dhara, P. Kalita, R. S. Narayanan, V. Chandrasekhar, B. Sarkar and A. Jana, Chem. Sci., 2019, 10, 4077
DOI: 10.1039/C8SC05477K

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