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Issue 3, 2010
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Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with simple arenes using sodium persulfate

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Abstract

We report a mild and efficient Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with a range of simple arenes using sodium persulfate (Na2S2O8). This green strategy generates biaryl C–C bonds from two unactivated sp2 hybridized C–H bonds. Electron-rich and electron-neutral arenes underwent oxidative arylation under our optimized reaction conditions. In substrates bearing two reactive ortho C–H bonds, selective diarylation via quadruple C–H bond functionalization was possible. The same reaction conditions were extended to an intramolecular cross-coupling for preparing lactams. The synthesis of relevant trifluoroacetate-bridged bimetallic Pd complexes derived from anilides and their stoichiometric reactivity were investigated.

Graphical abstract: Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with simple arenes using sodium persulfate

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Publication details

The article was received on 17 Mar 2010, accepted on 05 May 2010 and first published on 18 Jun 2010


Article type: Edge Article
DOI: 10.1039/C0SC00231C
Chem. Sci., 2010,1, 331-336

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    Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with simple arenes using sodium persulfate

    C. S. Yeung, X. Zhao, N. Borduas and V. M. Dong, Chem. Sci., 2010, 1, 331
    DOI: 10.1039/C0SC00231C

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