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Issue 2, 2019
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Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation

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Abstract

Cross-coupling of aryl compounds is one of the most powerful carbon–carbon bond forming reactions available. However, the vast majority employ scarce and expensive transition metal salts, in combination with high temperatures and long reaction times. Herein, we report a new, metal-free biaryl coupling that includes photoactivation of π-conjugated triazenes, in the presence of unactivated arenes, carried out at room temperature. Key experiments and theoretical calculations, to elucidate mechanistic details of this new, direct and significantly milder synthetic approach are presented.

Graphical abstract: Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation

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Article information


Submitted
29 Aug 2018
Accepted
22 Oct 2018
First published
22 Oct 2018

Org. Chem. Front., 2019,6, 152-161
Article type
Research Article
Author version available

Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation

E. Barragan, A. Noonikara Poyil, C. Yang, H. Wang and A. Bugarin, Org. Chem. Front., 2019, 6, 152
DOI: 10.1039/C8QO00938D

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