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In case of CuAAC transformation, the copper complex 7 was
applied to the reaction four times, giving 67% of isolated
product 11 in the fourth run. A signicant decrease in the
recovery of initiator 7 was observed for Glaser-type homo-
coupling. In each run, the product 25 was obtained with lower
yield, giving in the third time only 34% of the desired
compound 25. In the fourth run, the product 25 was not
detected. This outcome might be a consequence of the deacti-
vation of the copper initiator 7 under Glaser reaction conditions
aer longer time of use.
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In summary, the synthesis of easy accessible novel water-
soluble copper complex containing theophylline moiety has
been presented. The catalyst bearing ammonium functionali-
zation displayed high activity in three component click reaction
and in Glaser homo-coupling reaction under mild conditions. A
broad range of 1,4-substituted triazoles and 1,3-diynes have
been formed by the incorporation of 1 mol% of new simple
copper complex at room temperature in water. Presented cata-
lytic system is a good example of sustainable approach due to its
ability to be recycle up to fourth times in water in three
component click reaction. In case of Glaser homo-coupling
reaction, the novel initiator allows to obtain the expected
homo-dimer only three times, however in each run with
diminished yield. Further investigations into the utility of this
new water-soluble copper complex bearing theophylline moiety
in other catalytic reactions are in progress.
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8 (a) J. Garcıa-Alvarez, J. Dıez and J. Gimeno, Green Chem.,
2010, 12, 2127; (b) D. Wang, N. Li, M. Zhao, W. Shi, C. Ma
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and B. Chen, Green Chem., 2010, 12, 2120; (c) S. Dıez-
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Gonzalez, A. Correa, L. Cavallo and S. P. Nolan, Chem.–Eur.
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J., 2006, 12, 7558; (d) S. Dıez-Gonzalez, E. C. Escudero-
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Acknowledgements
Adan, J. Benet-Buchholz, E. D. Stevens, A. M. Z. Slawin and
S. P. Nolan, Dalton Trans., 2010, 39, 7595; (e) B. Liu,
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Authors gratefully acknowledge nancial support from the
National Science Centre (DEC-2012/07/D/ST5/02260). R. P.
thanks Warsaw Consortium of Academic Chemistry for KNOW
scholarship. The study was carried out at the Biological and
Chemical Research Centre, University of Warsaw, established
within the project co-nanced by European Union from the
European Regional Development Fund under the Operational
Programme Innovative Economy, 2007–2013.
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44252 | RSC Adv., 2016, 6, 44248–44253
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