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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Main Authors: Biswadip Banerji, K. Chandrasekhar, Sunil Kumar Killi, Sumit Kumar Pramanik, Pal Uttam, Sudeshna Sen, Nakul Chandra Maiti
Format: Article
Language:English
Published: The Royal Society 2016-01-01
Series:Royal Society Open Science
Subjects:
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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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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AT kchandrasekhar silvercatalysedazidealkynecycloadditionagaacassessingthemechanismbydensityfunctionaltheorycalculations
AT sunilkumarkilli silvercatalysedazidealkynecycloadditionagaacassessingthemechanismbydensityfunctionaltheorycalculations
AT sumitkumarpramanik silvercatalysedazidealkynecycloadditionagaacassessingthemechanismbydensityfunctionaltheorycalculations
AT paluttam silvercatalysedazidealkynecycloadditionagaacassessingthemechanismbydensityfunctionaltheorycalculations
AT sudeshnasen silvercatalysedazidealkynecycloadditionagaacassessingthemechanismbydensityfunctionaltheorycalculations
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