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Issue 19, 2018
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Quinoxaline as an integrated directing group in palladium-catalyzed ortho-C–H bond arylation of the aryl unit of 2-arylquinoxalines

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Abstract

We report the Pd-catalyzed C–H bond arylation at the ortho-position of the aryl unit of 2-arylquinoxalines. The reaction proceeds with complete regioselectivity using phosphine-free Pd(OAc)2 as the catalyst and potassium acetate as inexpensive base. In contrast to previously employed directing groups, quinoxaline is an integrated directing group in the final product that only promotes ortho-mono-arylation without the formation of bis-arylated products. A wide variety of (hetero)aryl bromides, including bromopyridine derivatives, has been successfully employed.

Graphical abstract: Quinoxaline as an integrated directing group in palladium-catalyzed ortho-C–H bond arylation of the aryl unit of 2-arylquinoxalines

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Article information


Submitted
31 May 2018
Accepted
21 Aug 2018
First published
22 Aug 2018

New J. Chem., 2018,42, 16036-16039
Article type
Paper

Quinoxaline as an integrated directing group in palladium-catalyzed ortho-C–H bond arylation of the aryl unit of 2-arylquinoxalines

I. Idris, F. Derridj, T. Roisnel, H. Doucet and J. Soulé, New J. Chem., 2018, 42, 16036
DOI: 10.1039/C8NJ02713G

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