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Molecules 2018, 23(9), 2145; https://doi.org/10.3390/molecules23092145

Transition-Metal-Free Activation of Amide Bond by Arynes

School of Pharmacy, Hyogo University of Health Sciences, Minatojima 1-3-6, Chuo-ku, Kobe 650-8530, Japan
Received: 3 August 2018 / Revised: 20 August 2018 / Accepted: 24 August 2018 / Published: 27 August 2018
(This article belongs to the Special Issue Amide Bond Activation)
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Abstract

Highly reactive arynes activate the N–C and C=O bonds of amide groups under transition metal-free conditions. This review highlights the insertion of arynes into the N–C and C=O bonds of the amide group. The insertion of arynes into the N–C bond gives the unstable four-membered ring intermediates, which are easily converted into ortho-disubstituted arenes. On the other hand, the selective insertion of arynes into the C=O bond is observed when the sterically less-hindered formamides are employed to give a reactive transient intermediate. Therefore, the trapping reactions of transient intermediates with a variety of reactants lead to the formation of oxygen atom-containing heterocycles. As relative functional groups are activated, the reactions of arynes with sulfinamides, phosphoryl amides, cyanamides, sulfonamides, thioureas, and vinylogous amides are also summarized. View Full-Text
Keywords: amide; arynes; insertion; activation; heterocycles; organic synthesis; multi-component coupling reaction amide; arynes; insertion; activation; heterocycles; organic synthesis; multi-component coupling reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Miyabe, H. Transition-Metal-Free Activation of Amide Bond by Arynes. Molecules 2018, 23, 2145.

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