M. Chetia, M. Konwar, B. Pegu et al.
Journal of Molecular Structure 1233 (2021) 130019
Table 5
Comparative study of our catalytic systems with the literature reports.
Entry
1
Reaction condition for 1,2,3-triazole synthesis
Yields(%)
Reference
This work
Cu(I)-polyaniline, H2O:EG (1:1), RT, 1-6 h i) Azide-alkyne cycloaddition ii)
One pot azide-alkyne cycloaddition Cu(I)-polyaniline, H2O:EG (1:1), RT, 1-6
h, Ascorbic acid iii) One pot azide-alkyne cycloaddition from boronic acids
Cu(I)-polyaniline, water, 100°C (One pot azide-alkyne cycloaddition)
Cu(I)-Zeolite, toluene, RT, 15 h
50-9550-9050-90
2
3
4
5
6
79-92
59-94
78-99
78-89
71-98
Cu(OH)x/TiO2, toluene, 60°C, Ar atmosphere
Cu(II)-hydrotalcite, CH3CN, RT, 6-12 h
Cu NPs@Hydrotalcite, ethylene glycol, RT, 1-3 h (Azide-alkyne cycloaddition
only)
7
8
9
CuI-Amberlyst A-21, CH3CN:CH2Cl2, RT, 1-24 h
70-99
65
Cu/C (10 mol%), dioxane, RT, 48 h
Aminomethyl polystyrene-supported copper(I) catalyst (Cu(I)-AMPS), water,
RT, 1-2 h (Azide-alkyne cycloaddition only)
80-98
10
11
Cellulose–copper, water, RT, 1-12 h (Azide-alkyne cycloaddition only)
Ionic-liquid and cuprous sulfite containing halloysite nanoclay, water, RT, 1 h
(One pot azide-alkyne cycloaddition)
82-96
85-95
Conclusions
We demonstrated that Cu-PANI can serve as efficient heteroge-
neous catalyst for synthesizing a library of 1,4-disubstituted-1,2,3-
triazoles through azide-alkyne cycloaddition and one-pot click re-
action. Use of water as solvent and room temperature reaction
condition makes it a benign system. The easy recoverability and
reusability of the polymer supported catalysts prove the hetero-
geneity of the system. The redox active nature of PANI played a
vital role in synthesizing the Cu(I) form of the catalyst which in
turn catalyzed the click reactions exceptionally well. Thus, it is ex-
pected that Cu-PANI catalyst will be applicable in greater prospects
in various scientific areas.
Supporting information: The Supporting Information contains
experimental procedure, NMR spectra for all compounds with full
characterization data.
Declaration of Competing Interest
The authors declare no competing financial interest.
CRediT authorship contribution statement
Mitali Chetia: Conceptualization, Methodology, Writing - orig-
inal draft. Manashjyoti Konwar: Conceptualization, Methodology,
Software, Data curation, Investigation, Writing - original draft.
Biswajit Pegu: Visualization, Data curation, Investigation. Surajit
Konwer: Supervision, Data curation, Writing - review & editing.
Diganta Sarma: Supervision, Writing - review & editing, Software,
Validation.
Acknowledgement
Scheme 3. Plausible reaction mechanism.
D. S. is thankful to DST, New Delhi, India for a research grant
[No. EMR/2016/002345]. The authors also acknowledge the De-
partment of Science and Technology for financial assistance under
DST-FIST programme and UGC, New Delhi for Special Assistance
Programme (UGC-SAP) to the Department of Chemistry, Dibrugarh
University.
tants are not inevitably required to get the high polymer mate-
rials. 1,2,3-triazoles were synthesized using these two newly syn-
thesized Cu-PANI catalysts though three different approaches- (i)
azide-alkyne cycloaddition; (ii) one pot click reaction; (iii) from
boronic acids at room temperature using water as a solvent. To the
best of our knowledge, Cu-PANI catalyst has been used for the first
time for one-pot 1,2,3-triazoles synthesis from boronic acid sources
at room temperature and water as a solvent. This indicates that
unlike other heterogeneous catalysts (as mentioned in Table 5), our
protocol can be applied to the synthesis of a large number of 1,2,3-
triazoles from different starting materials through environmentally
benign manner.
Supplementary materials
Supplementary material associated with this article can be
References
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