Transition-Metal-Free Activation of Amide Bond by Arynes
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-...
Main Author: | |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2018-08-01
|
Series: | Molecules |
Subjects: | |
Online Access: | http://www.mdpi.com/1420-3049/23/9/2145 |
id |
doaj-f606db986b30488a8579aa32f00ee20e |
---|---|
record_format |
Article |
spelling |
doaj-f606db986b30488a8579aa32f00ee20e2020-11-25T02:17:27ZengMDPI AGMolecules1420-30492018-08-01239214510.3390/molecules23092145molecules23092145Transition-Metal-Free Activation of Amide Bond by ArynesHideto Miyabe0School of Pharmacy, Hyogo University of Health Sciences, Minatojima 1-3-6, Chuo-ku, Kobe 650-8530, JapanHighly 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.http://www.mdpi.com/1420-3049/23/9/2145amidearynesinsertionactivationheterocyclesorganic synthesismulti-component coupling reaction |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Hideto Miyabe |
spellingShingle |
Hideto Miyabe Transition-Metal-Free Activation of Amide Bond by Arynes Molecules amide arynes insertion activation heterocycles organic synthesis multi-component coupling reaction |
author_facet |
Hideto Miyabe |
author_sort |
Hideto Miyabe |
title |
Transition-Metal-Free Activation of Amide Bond by Arynes |
title_short |
Transition-Metal-Free Activation of Amide Bond by Arynes |
title_full |
Transition-Metal-Free Activation of Amide Bond by Arynes |
title_fullStr |
Transition-Metal-Free Activation of Amide Bond by Arynes |
title_full_unstemmed |
Transition-Metal-Free Activation of Amide Bond by Arynes |
title_sort |
transition-metal-free activation of amide bond by arynes |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2018-08-01 |
description |
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. |
topic |
amide arynes insertion activation heterocycles organic synthesis multi-component coupling reaction |
url |
http://www.mdpi.com/1420-3049/23/9/2145 |
work_keys_str_mv |
AT hidetomiyabe transitionmetalfreeactivationofamidebondbyarynes |
_version_ |
1724886308387553280 |