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Ru(II)-catalyzed ortho-amidation and decarboxylation of aromatic acids: a versatile route to meta-substituted N-aryl benzamides

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Abstract

Carboxylate as a promising and valuable directing group has attracted a great deal of attention. However, employing it as a traceless direction group has rarely been reported. We developed the ruthenium-catalyzed amidation of substituted benzoic acids with isocyanates via directed C-H functionalization followed by decarboxylation to afford the corresponding meta-substituted N-aryl benzamides, in which the carboxylate serves as a unique, removable directing group. Notably, this protocol can provide an efficient alternative to access meta-substituted N-aryl benzamides, which are much more difficult to prepare than ortho-substituted analogues.

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Authors and Affiliations

  1. Key Laboratory of Applied Surface and Colloid Chemistry (Ministry of Education); Key Laboratory for Macromolecular Science of Shaanxi Province; School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, China

    Xian-Ying Shi, Xue-Fen Dong, Juan Fan, Ke-Yan Liu & Jun-Fa Wei

  2. Department of Chemistry, McGill University, Montreal, QC, H3A 0B8, Canada

    Chao-Jun Li

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  1. Xian-Ying Shi
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  2. Xue-Fen Dong
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  3. Juan Fan
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  4. Ke-Yan Liu
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  5. Jun-Fa Wei
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  6. Chao-Jun Li
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Correspondence to Xian-Ying Shi or Chao-Jun Li.

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Shi, XY., Dong, XF., Fan, J. et al. Ru(II)-catalyzed ortho-amidation and decarboxylation of aromatic acids: a versatile route to meta-substituted N-aryl benzamides. Sci. China Chem. 58, 1286–1291 (2015). https://doi.org/10.1007/s11426-015-5364-3

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