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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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Publication details

The article was received on 31 May 2018, accepted on 21 Aug 2018 and first published on 22 Aug 2018


Article type: Paper
DOI: 10.1039/C8NJ02713G
Citation: New J. Chem., 2018,42, 16036-16039

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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

    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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