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Issue 13, 2017
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Palladium-catalyzed interannular meta-C–H arylation

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Abstract

The interannular meta-selective C–H arylation of biaryl-2-trifluoroacetamides using Pd(II)/norbornene catalysis is reported. The installation of a trifluoroacetyl protecting group to tune their electronic properties and binding ability is essential for interannular selectivity. A dimeric palladacycle, comprising two cyclopalladated trifluoroacetamino biaryl units linked through trifluoroacetamide, was isolated and confirmed to be the key intermediate. Furthermore, the resulting products could be further elaborated via ipso-alkynylation and/or directed intraannular ortho-C–H functionalization, allowing access to various fully functionalized biaryl-2-amine derivatives.

Graphical abstract: Palladium-catalyzed interannular meta-C–H arylation

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Publication details

The article was received on 06 Jan 2017, accepted on 20 Jan 2017 and first published on 23 Jan 2017


Article type: Communication
DOI: 10.1039/C7CC00110J
Citation: Chem. Commun., 2017,53, 2166-2169
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    Palladium-catalyzed interannular meta-C–H arylation

    P. Ling, K. Chen and B. Shi, Chem. Commun., 2017, 53, 2166
    DOI: 10.1039/C7CC00110J

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