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Issue 24, 2016
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Chemoselective reduction of carboxamides

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Abstract

The reduction of amides gives access to a wide variety of important compounds such as amines, imines, enamines, nitriles, aldehydes and alcohols. The chemoselective transformation into these functional groups is challenging due to the intrinsic stability of the amide bond; nevertheless, the ability to reduce highly stable carboxamides selectively in the presence of sensitive functional groups is of high synthetic value for academic and industrial chemists. Hydride-based reagents such as LiAlH4 or diboranes are today the most commonly used compounds for amide reductions, and apart from the substantial amount of waste generated using these methods, they lack tolerance to most other functional groups. This tutorial review provides an overview of the recent progress made in the development of chemoselective protocols for amide reduction and gives an insight to their advantages and drawbacks.

Graphical abstract: Chemoselective reduction of carboxamides

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Publication details

The article was received on 22 Mar 2016 and first published on 24 Oct 2016


Article type: Tutorial Review
DOI: 10.1039/C6CS00244G
Chem. Soc. Rev., 2016,45, 6685-6697

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    Chemoselective reduction of carboxamides

    A. Volkov, F. Tinnis, T. Slagbrand, P. Trillo and H. Adolfsson, Chem. Soc. Rev., 2016, 45, 6685
    DOI: 10.1039/C6CS00244G

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