Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations
‘Click reactions’ are the copper catalysed dipolar cycloaddition reaction of azides and alkynes to incorporate nitrogens into a cyclic hydrocarbon scaffold forming a triazole ring. Owing to its efficiency and versatility, this reaction and the products, triazole-containing heterocycles, have immense...
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The Royal Society
2016-01-01
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Series: | Royal Society Open Science |
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Online Access: | https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.160090 |
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author | Biswadip Banerji K. Chandrasekhar Sunil Kumar Killi Sumit Kumar Pramanik Pal Uttam Sudeshna Sen Nakul Chandra Maiti |
author_facet | Biswadip Banerji K. Chandrasekhar Sunil Kumar Killi Sumit Kumar Pramanik Pal Uttam Sudeshna Sen Nakul Chandra Maiti |
author_sort | Biswadip Banerji |
collection | DOAJ |
description | ‘Click reactions’ are the copper catalysed dipolar cycloaddition reaction of azides and alkynes to incorporate nitrogens into a cyclic hydrocarbon scaffold forming a triazole ring. Owing to its efficiency and versatility, this reaction and the products, triazole-containing heterocycles, have immense importance in medicinal chemistry. Copper is the only known catalyst to carry out this reaction, the mechanism of which remains unclear. We report here that the ‘click reactions’ can also be catalysed by silver halides in non-aqueous medium. It constitutes an alternative to the well-known CuAAC click reaction. The yield of the reaction varies on the type of counter ion present in the silver salt. This reaction exhibits significant features, such as high regioselectivity, mild reaction conditions, easy availability of substrates and reasonably good yields. In this communication, the findings of a new catalyst along with the effect of solvent and counter ions will help to decipher the still obscure mechanism of this important reaction. |
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issn | 2054-5703 |
language | English |
last_indexed | 2024-12-22T17:10:40Z |
publishDate | 2016-01-01 |
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spelling | doaj.art-caa851c1fbf945a2ac53fa2313defabc2022-12-21T18:19:05ZengThe Royal SocietyRoyal Society Open Science2054-57032016-01-013910.1098/rsos.160090160090Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculationsBiswadip BanerjiK. ChandrasekharSunil Kumar KilliSumit Kumar PramanikPal UttamSudeshna SenNakul Chandra Maiti‘Click reactions’ are the copper catalysed dipolar cycloaddition reaction of azides and alkynes to incorporate nitrogens into a cyclic hydrocarbon scaffold forming a triazole ring. Owing to its efficiency and versatility, this reaction and the products, triazole-containing heterocycles, have immense importance in medicinal chemistry. Copper is the only known catalyst to carry out this reaction, the mechanism of which remains unclear. We report here that the ‘click reactions’ can also be catalysed by silver halides in non-aqueous medium. It constitutes an alternative to the well-known CuAAC click reaction. The yield of the reaction varies on the type of counter ion present in the silver salt. This reaction exhibits significant features, such as high regioselectivity, mild reaction conditions, easy availability of substrates and reasonably good yields. In this communication, the findings of a new catalyst along with the effect of solvent and counter ions will help to decipher the still obscure mechanism of this important reaction.https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.160090triazoleag-catalystclick reactioncycloadditiondft |
spellingShingle | Biswadip Banerji K. Chandrasekhar Sunil Kumar Killi Sumit Kumar Pramanik Pal Uttam Sudeshna Sen Nakul Chandra Maiti Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations Royal Society Open Science triazole ag-catalyst click reaction cycloaddition dft |
title | Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations |
title_full | Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations |
title_fullStr | Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations |
title_full_unstemmed | Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations |
title_short | Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations |
title_sort | silver catalysed azide alkyne cycloaddition agaac assessing the mechanism by density functional theory calculations |
topic | triazole ag-catalyst click reaction cycloaddition dft |
url | https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.160090 |
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