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Direct C–H heteroarylation by an acenaphthyl-based α-diimine palladium complex: improvement of the reaction efficiency for bi(hetero)aryls under aerobic conditions

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Abstract

A bulky ancenaphthyl skeleton-based α-diimine palladium complex with ortho-tert-butyl on N-aryl moieties was designed, synthesized and characterized. The developed palladium complex was applied for direct C–H arylation under aerobic reaction conditions. A range of heteroaryls, such as thiozoles, thiophenes, furans, imidazopyridines, indolizines, isoxazoles, imidazoles, triazoles, pyrazoles, indoles, pyrroles and pyrazolidinones, were used, while various coupling partners of heteroaryl bromides with wide functional groups were compatible. Upon using 0.1–0.05 mol% of a precatalyst, more than 90 examples of cross-coupling products were afforded in good to excellent yields, demonstrating that this phosphine-free catalytic system scaffold enables a general access to biheteroaryls.

Graphical abstract: Direct C–H heteroarylation by an acenaphthyl-based α-diimine palladium complex: improvement of the reaction efficiency for bi(hetero)aryls under aerobic conditions

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Publication details

The article was received on 07 Jul 2017, accepted on 25 Aug 2017 and first published on 28 Aug 2017


Article type: Research Article
DOI: 10.1039/C7QO00562H
Citation: Org. Chem. Front., 2017, Advance Article
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    Direct C–H heteroarylation by an acenaphthyl-based α-diimine palladium complex: improvement of the reaction efficiency for bi(hetero)aryls under aerobic conditions

    F. Chen, F. Huang, X. Yao, T. Li and F. Liu, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00562H

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