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Decarbonylative cross-coupling of amides

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Abstract

Cross-coupling reactions are among the most powerful C–C and C–X bond forming tools in organic chemistry. Traditionally, cross-coupling methods rely on the use of aryl halides or pseudohalides as electrophiles. In the past three years, decarbonylative cross-couplings of amides have emerged as an attractive method for the construction of a wide variety of carbon–carbon and carbon–heteroatom bonds, allowing for the synthetically-valuable functional group inter-conversion of the amide bond. These previously elusive reactions hinge upon selective activation of the N–C(O) acyl amide bond, followed by CO extrusion, in a formal double N–C/C–C bond activation, to generate a versatile aryl–metal intermediate as an attractive alternative to traditional cross-couplings of aryl halides and pseudohalides. In this perspective review, we present recent advances and key developments in the field of decarbonylative cross-coupling reactions of amides as well as discuss future challenges and potential applications for this exciting field.

Graphical abstract: Decarbonylative cross-coupling of amides

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Publication details

The article was received on 29 Jul 2018, accepted on 02 Oct 2018 and first published on 03 Oct 2018


Article type: Review Article
DOI: 10.1039/C8OB01832D
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Decarbonylative cross-coupling of amides

    C. Liu and M. Szostak, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01832D

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