Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


IMPACT FACTOR 2018: 2.350
5-year IMPACT FACTOR: 4.037

CiteScore 2018: 4.66

SCImago Journal Rank (SJR) 2018: 1.240
Source Normalized Impact per Paper (SNIP) 2018: 1.826

Online
ISSN
1365-3075
See all formats and pricing
More options …
Volume 91, Issue 4

Issues

Synthesis of polymacrocyclic compounds via Pd-catalyzed amination and evaluation of their derivatives as metal detectors

Macrocycles and detectors

Alexei D. Averin / Irina P. Beletskaya
Published Online: 2019-03-15 | DOI: https://doi.org/10.1515/pac-2018-0714

Abstract

A mini-review is dedicated to the application of Pd(0)-catalyzed amination reactions for the synthesis of polymacrocyclic compounds of various architectures. Such molecules comprise diazacrown ether moieties or structural fragments of tri- and tetraazamacrocycles, polyamine or polyoxadiamine chains of different length and aromatic spacers. Polymacrocyclic compounds thus formed possess an increased number of coordination sites and are suitable for testing as potential receptors of metal cations. Some of these macrocyclic compounds were decorated with the exocyclic dansyl fluorophore group or were coupled with porphyrin units to form polymacrocyclic conjugates. Fluorescent spectra of these compounds were studied in the presence of various metal perchlorates and several macrocycles were found to act as chemosensors or molecular probes for such cations like Cu(II), Al(III), Cr(III).

Keywords: catalysis; cross-coupling reactions; cryptands; detection; Distinguished Women in Chemistry and Chemical Engineering; fluorescence; macrocycles; palladium; porphyrins

References

  • [1]

    E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A. Abu El-Fadl, D. N. Reinhoudt. J. Am. Chem. Soc. 112, 6979 (1990).CrossrefGoogle Scholar

  • [2]

    J. Zavada, J. Koudelka, P. Holy, M. Belohradsky, I. Stibor. Coll. Czech. Chem. Commun. 54, 1043 (1989).CrossrefGoogle Scholar

  • [3]

    J. Bouquant, A. Delville, J. Grandjean, P. Laszlo. J. Am. Chem. Soc. 104, 686 (1982).CrossrefGoogle Scholar

  • [4]

    R. C. Helgeson, T. L. Tarnowski, D. J. Cram. J. Org. Chem. 44, 2538 (1979).CrossrefGoogle Scholar

  • [5]

    S. F. Lincoln, A. Abou-Hamdan. Inorg. Chem. 29, 3584 (1990).CrossrefGoogle Scholar

  • [6]

    F. H. Kohnke, J. F. Stoddart. J. Chem. Soc. Chem. Commun. 314 (1985).Google Scholar

  • [7]

    E. Chapoteau, B. P. Czech, A. Kumar, A. Pose. J. Incl. Phenom. 6, 41 (1988).CrossrefGoogle Scholar

  • [8]

    A. Wallon, J. Peter-Katalinic, U. Werner, W. M. Muller, F. Vogtle. Chem. Ber. 123, 375 (1990).CrossrefGoogle Scholar

  • [9]

    J. M. Lehn, J. Simon, A. Moradpour. Helv. Chim. Acta. 61, 2407 (1978).CrossrefGoogle Scholar

  • [10]

    Y. Murakami, J. Kikuchi, T. Ohno, T. Hirayama. Chem. Lett. 18, 881 (1989).CrossrefGoogle Scholar

  • [11]

    A.-M. Albrecht-Gary, C. O. Dietrich-Buchecker, Z. Saad, J.-P. Sauvage, J. Weiss. J. Chem. Soc. Chem. Commun. 1325 (1986).Google Scholar

  • [12]

    R. M. Izatt, K. Pawlak, J. S. Bradshaw, R. L. Bruening. Chem. Rev. 91, 1721 (1991).CrossrefGoogle Scholar

  • [13]

    J. L. Bourque, P. D. Boyle, K. M. Baines. Chem. Eur. J. 21, 9790 (2015).CrossrefGoogle Scholar

  • [14]

    J. Pitarch-Jarque, R. Belda, F. Lloret, J. Ferrando-Soria, P. Navarro, A. Lopera, E. García-España. Dalton Trans. 44, 3378 (2015).CrossrefGoogle Scholar

  • [15]

    K. V. Tan, P. A. Pellegrini, B. W. Skelton, C. F. Hogan, I. Greguric, P. J. Barnard. Inorg. Chem. 53, 468 (2014).CrossrefGoogle Scholar

  • [16]

    D. Over, X. Zeng, C. Bornholdt, J. Marrot, O. Reinaud. Inorg. Chem. 52, 14089 (2013).CrossrefGoogle Scholar

  • [17]

    G. X. Jin, M. D. Bailey, M. J. Allen. Inorg. Chem. 55, 9085 (2016).CrossrefGoogle Scholar

  • [18]

    R. F. Zhang, W. J. Hu, Y. A. Liu, X. L. Zhao, J. S. Li, B. Jiang, K. Wen. J. Org. Chem. 81, 5649 (2016).CrossrefGoogle Scholar

  • [19]

    J. F. Xu, Y. Z. Chen, L. Z. Wu, C. H. Tung, Q. Z. Yang. Org. Lett. 16, 684 (2014).CrossrefGoogle Scholar

  • [20]

    Y. Habata, M. Ikeda, A. K. Sah, K. Noto, S. Kuwahara. Inorg. Chem. 52, 11697 (2013).CrossrefGoogle Scholar

  • [21]

    G. Y. Xie, L. Jiang, T. B. Lu. Dalton Trans. 42, 14092 (2013).CrossrefGoogle Scholar

  • [22]

    X. Ji, M. Zhang, X. Yan, J. Li, F. Huang. Chem. Commun. 49, 1178 (2013).CrossrefGoogle Scholar

  • [23]

    A. Lélias-Vanderperre, J. C. Chambron, E. Espinosa, P. Terrier, E. Leize-Wagner. Org. Lett. 9, 2961 (2007).CrossrefGoogle Scholar

  • [24]

    Y. Nakahara, T. Kida, Y. Nakatsuji, M. Akashi. Org. Biomol. Chem. 3, 1787 (2005).CrossrefGoogle Scholar

  • [25]

    A. Brown, T. Bunchuay, C. Crane, N. White, A. Thompson, P. D. Beer. Chem. Eur. J. 24, 1 (2018).CrossrefGoogle Scholar

  • [26]

    S. Chakraborty, S. Saha, L. M. P. Lima, U. Warzok, S. Sarkar, B. Akhuli, M. Nandi, S. Bej, N. N. Adarsh, C. A. Schalley, R. Delgado, P. Ghosh. J. Org. Chem. 82, 10007 (2017).CrossrefGoogle Scholar

  • [27]

    S. Porwanski, F. Moretti, F. Dumarcay-Charbonnier, A. Marsura. Ann. Pharm. Fr. 74, 198 (2016).CrossrefGoogle Scholar

  • [28]

    J. Pitarch-Jarque, R. Belda, L. García-España, J. M. Llinares, F. Pan, K. Rissanen, P. Navarro, E. García-España. Dalton Trans. 44, 7761 (2015).CrossrefGoogle Scholar

  • [29]

    P. Mateus, R. Delgado, V. André, M. Teresa Duarte. Org. Biomol. Chem. 13, 834 (2015).CrossrefGoogle Scholar

  • [30]

    E. Brunetti, A. Inthasot, F. Keymeulen, O. Reinaud, I. Jabin, K. Bartik. Org. Biomol. Chem. 13, 2931 (2015).CrossrefGoogle Scholar

  • [31]

    J. Li, D. Yim, W. D. Jang, J. Yoon. Chem. Soc. Rev. 46, 2437 (2017).CrossrefGoogle Scholar

  • [32]

    M. Denis, J. Pancholi, K. Jobe, M. Watkinson, S. M. Goldup. Angew. Chem. Int. Ed. 57, 5310 (2018).CrossrefGoogle Scholar

  • [33]

    M. Cheng, J. Zhang, X. Ren, S. Guo, T. Xiao, X. Y. Hu, J. Jiang, L. Wang. Chem. Commun. 53, 11838 (2017).CrossrefGoogle Scholar

  • [34]

    N. Kon, H. Takemura, K. Otsuka, K. Tanoue, S. Nakashima, M. Yasutake, K. Tani, J. Kimoto, T. Shinmyozu, T. Inazu. J. Org. Chem. 65, 3708 (2000).CrossrefGoogle Scholar

  • [35]

    T. L. Price Jr., H. R. Wessels, C. Slebodnick, H. W. Gibson. J. Org. Chem. 82, 8117 (2017).CrossrefGoogle Scholar

  • [36]

    H. Struthers, T. L. Mindt, R. Schibli. Dalton Trans. 39, 675 (2010).CrossrefGoogle Scholar

  • [37]

    I. P. Beletskaya, A. D. Averin, A. G. Bessmertnykh, F. Denat, R. Guilard. Russ. J. Org. Chem. 46, 947 (2010).CrossrefGoogle Scholar

  • [38]

    A. D. Averin, S. M. Kobelev, M. V. Anokhin, A. G. Bessmertnykh Lemeune, R. Guilard, I. P. Beletskaya. in Targets in Heterocyclic Systems: Chemistry and Properties, Vol. 15. O. A. Attanasi, D. Spinelli (Eds.), pp. 193–225 (2011).Google Scholar

  • [39]

    A. D. Averin, A. V. Shukhaev, S. L. Golub, A. K. Buryak, I. P. Beletskaya. Synthesis 2995 (2007).Google Scholar

  • [40]

    A. D. Averin, A. N. Uglov, I. P. Beletskaya. Chem. Lett. 37, 1074 (2008).CrossrefGoogle Scholar

  • [41]

    I. P. Beletskaya, A. D. Averin, A. G. Bessmertnykh, R. Guilard. Tetrahedron Lett. 42, 4983 (2001).CrossrefGoogle Scholar

  • [42]

    I. P. Beletskaya, A. D. Averin, N. A. Pleshkova, A. A. Borisenko, M. V. Serebryakova, F. Denat, R. Guilard. Synlett 87 (2005).Google Scholar

  • [43]

    I. P. Beletskaya, A. D. Averin, O. A. Ulanovskaya, I. A. Fedotenko, A. A. Borisenko, M. V. Serebryakova, F. Denat, R. Guilard. Chem. Lett. 34, 1100 (2005).CrossrefGoogle Scholar

  • [44]

    A. D. Averin, A. N. Uglov, A. K. Buryak, A. G. Bessmertnykh, R. Guilard, I. P. Beletskaya. Heterocycles 80, 957 (2010).CrossrefGoogle Scholar

  • [45]

    A. D. Averin, E. R. Ranyuk, N. V. Lukashev, S. L. Golub, A. K. Buryak, I. P. Beletskaya. Tetrahedron Lett. 49, 1188 (2008).CrossrefGoogle Scholar

  • [46]

    E. Ranyuk, C. Morkos-Douaihy, A. Bessmertnykh, F. Denat, A. Averin, I. Beletskaya, R. Guilard. Org. Lett. 11, 987 (2009).CrossrefGoogle Scholar

  • [47]

    E. Ranyuk, A. Uglov, M. Meyer, A. Bessmertnykh Lemeune, F. Denat, A. Averin, I. Beletskaya, R. Guilard. Dalton Trans. 40, 10491 (2011).CrossrefGoogle Scholar

  • [48]

    A. S. Abel, A. D. Averin, I. P. Beletskaya. New J. Chem. 40, 5818 (2016).CrossrefGoogle Scholar

  • [49]

    A. S. Abel, A. Yu. Mitrofanov, Y. Rousselin, F. Denat, A. Bessmertnykh-Lemeune, A. D. Averin, I. P. Beletskaya. ChemPlusChem. 81, 35 (2016).CrossrefGoogle Scholar

  • [50]

    O. K. Grigorova, A. D. Averin, O. A. Maloshitskaya, I. P. Beletskaya. Macroheterocycles 9, 425 (2016).CrossrefGoogle Scholar

  • [51]

    O. K. Grigorova, A. D. Averin, O. A. Maloshitskaya, I. P. Beletskaya. Macroheterocycles 10, 446 (2017).CrossrefGoogle Scholar

  • [52]

    A. D. Averin, A. V. Shukhaev, A. K. Buryak, F. Denat, R. Guilard, I. P. Beletskaya. Macroheterocycles 2, 281 (2009).CrossrefGoogle Scholar

  • [53]

    I. P. Beletskaya, A. D. Averin, A. G. Bessmertnykh, F. Denat, R. Guilard. Tetrahedron Lett. 43, 1193 (2002).CrossrefGoogle Scholar

  • [54]

    I. P. Beletskaya, A. G. Bessmertnykh, A. D. Averin, F. Denat, R. Guilard. Eur. J. Org. Chem. 281 (2005).Google Scholar

  • [55]

    M. V. Anokhin, A. D. Averin, A. K. Buryak, I. P. Beletskaya. Mendeleev Commun. 21, 132 (2011).CrossrefGoogle Scholar

  • [56]

    M. V. Anokhin, A. D. Averin, A. K. Buryak, I. P. Beletskaya. Russ. Chem. Bull. 60, 992 (2011).CrossrefGoogle Scholar

  • [57]

    A. A. Yakushev, M. V. Anokhin, A. D. Averin, O. A. Maloshitskaya, I. P. Beletskaya. Russ. Chem. Bull. 61, 1474 (2012).CrossrefGoogle Scholar

  • [58]

    S. M. Kobelev, A. D. Averin, A. K. Buryak, F. Denat, R. Guilard, I. P. Beletskaya. Macroheterocycles 7, 28 (2014).CrossrefGoogle Scholar

  • [59]

    A. D. Averin, A. N. Uglov, G. A. Zubrienko, E. A. Tarasenko, A. K. Buryak, I. P. Beletskaya. Curr. Org. Synth. 14, 918 (2017).Google Scholar

  • [60]

    A. N. Uglov, G. A. Zubrienko, A. S. Abel, A. D. Averin, O. A. Maloshitskaya, A. Bessmertnykh-Lemeune, F. Denat, I. P. Beletskaya. Heterocycles 88, 1213 (2014).CrossrefGoogle Scholar

  • [61]

    E. R. Ranyuk, A. D. Averin, I. P. Beletskaya. Adv. Synth. Catal. 352, 2299 (2010).CrossrefGoogle Scholar

  • [62]

    O. K. Grigorova, A. D. Averin, O. A. Maloshitskaya, V. B. Rybakov, I. P. Beletskaya. Macroheterocycles 9, 418 (2016).CrossrefGoogle Scholar

  • [63]

    A. A. Yakushev, N. M. Chernichenko, M. V. Anokhin, A. D. Averin, A. K. Buryak, F. Denat, I. P. Beletskaya. Molecules 19, 940 (2014).CrossrefGoogle Scholar

  • [64]

    N. M. Chernichenko, A. D. Averin, A. K. Buryak, I. P. Beletskaya. Russ. Chem. Bull. 63, 2056 (2014).CrossrefGoogle Scholar

  • [65]

    A. A. Yakushev, M. V. Anokhin, A. D. Averin, O. A. Maloshitskaya, E. N. Savelyev, G. M. Butov, B. S. Orlinson, I. A. Novakov, I. P. Beletskaya. Macroheterocycles 6, 40 (2013).CrossrefGoogle Scholar

  • [66]

    A. D. Averin, A. V. Shukhaev, A. K. Buryak, F. Denat, R. Guilard, I. P. Beletskaya. Tetrahedron Lett. 49, 3950 (2008).CrossrefGoogle Scholar

  • [67]

    A. D. Averin, K. S. Tyutenov, A. V. Shukhaev, S. M. Kobelev, A. K. Buryak, F. Denat, R. Guilard, I. P. Beletskaya. Heterocycles 86, 1341 (2012).CrossrefGoogle Scholar

  • [68]

    A. D. Averin, A. V. Shukhaev, A. I. Vovk, V. P. Kukhar, F. Denat, R. Guilard, I. P. Beletskaya. Macroheterocycles 7, 174 (2014).CrossrefGoogle Scholar

  • [69]

    S. M. Kobelev, A. D. Averin, A. K. Buryak, E. N. Savelyev, B. S. Orlinson, G. M. Butov, I. A. Novakov, F. Denat, R. Guilard, I. P. Beletskaya. ARKIVOC vii, 196 (2012).Google Scholar

  • [70]

    S. M. Kobelev, A. D. Averin, A. K. Buryak, A. I. Vovk, V. P. Kukhar, F. Denat, R. Guilard, I. P. Beletskaya. Heterocycles 90, 989 (2015).CrossrefGoogle Scholar

  • [71]

    S. M. Kobelev, A. D. Averin, A. K. Buryak, F. Denat, R. Guilard, I. P. Beletskaya. Heterocycles 82, 1447 (2011).Google Scholar

  • [72]

    S. M. Kobelev, A. D. Averin, O. A. Maloshitskaya, F. Denat, R. Guilard, I. P. Beletskaya. Macroheterocycles 5, 389 (2012).CrossrefGoogle Scholar

  • [73]

    N. M. Chernichenko, V. N. Shevchuk, A. D. Averin, O. A. Maloshitskaya, I. P. Beletskaya. Synlett 28, 2800 (2017).CrossrefGoogle Scholar

  • [74]

    A. D. Averin, N. M. Chernichenko, V. N. Shevchuk, O. A. Maloshitskaya, F. Denat, I. P. Beletskaya. Macroheterocycles 11, 141 (2018).CrossrefGoogle Scholar

  • [75]

    N. M. Chernichenko, A. D. Averin, I. P. Beletskaya. Lett. Org. Chem. 15, 425 (2018).CrossrefGoogle Scholar

  • [76]

    S. M. Kobelev, A. D. Averin, A. K. Buryak, F. Denat, R. Guilard, I. P. Beletskaya. Tetrahedron Lett. 53, 210 (2012).CrossrefGoogle Scholar

  • [77]

    S. M. Kobelev, A. D. Averin, A. K. Buryak, F. Denat, R. Guilard, I. P. Beletskaya. Macroheterocycles 7, 28 (2014).CrossrefGoogle Scholar

  • [78]

    A. A. Yakushev, A. D. Averin, O. A. Maloshitskaya, S. A. Syrbu, O. I. Koifman, I. P. Beletskaya. Macroheterocycles 9, 65 (2016).CrossrefGoogle Scholar

  • [79]

    A. A. Yakushev, A. D. Averin, O. A. Maloshitskaya, S. A. Syrbu, O. I. Koifman, I. P. Beletskaya. Mendeleev Commun. 26, 199 (2016).CrossrefGoogle Scholar

  • [80]

    A. A. Yakushev, A. D. Averin, O. A. Maloshitskaya, O. I. Koifman, S. A. Syrbu, I. P. Beletskaya. Macroheterocycles 11, 135 (2018).CrossrefGoogle Scholar

  • [81]

    A. D. Averin, A. A. Yakushev, O. A. Maloshitskaya, O. I. Koifman, S. A. Syrbu, I. P. Beletskaya. Russ. Chem. Bull. 66, 1456 (2017).CrossrefGoogle Scholar

About the article

Published Online: 2019-03-15

Published in Print: 2019-04-24


Funding Source: Russian Science Foundation

Award identifier / Grant number: N 14-23-00186P

Funding Source: Russian Foundation for Basic Research

Award identifier / Grant number: N 17-53-16012

The research was financially supported by the Russian Science Foundation, Funder Id: 10.13039/501100006769 (RSF grant N 14-23-00186P) and partially by the Russian Foundation for Basic Research, Funder Id: 10.13039/501100002261 (RFBR grant N 17-53-16012).


Citation Information: Pure and Applied Chemistry, Volume 91, Issue 4, Pages 633–651, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2018-0714.

Export Citation

©2019 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/.Get Permission

Comments (0)

Please log in or register to comment.
Log in