Synlett 2015; 26(11): 1437-1449
DOI: 10.1055/s-0034-1380699
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© Georg Thieme Verlag Stuttgart · New York

Click Metallodendrimers and Their Functions

Didier Astruc*
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
,
Roberto Ciganda
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
b   Facultad de Química de San Sebastián, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain
,
Christophe Deraedt
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
,
Sylvain Gatard
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
,
Liyuan Liang
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
,
Na Li
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
,
Catia Ornelas
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
c   Institute of Chemistry, University of Campinas, Campinas 13083-970, Sao Paulo, Brazil
,
Amalia Rapakousiou
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
,
Jaime Ruiz
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
,
Dong Wang
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
,
Yanlan Wang
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
,
Pengxiang Zhao
a   ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France   Email: d.astruc@ism.u-bordeaux1.fr
d   Nano Chemistry Group, Science and Technology on Surface Physics and Chemistry Laboratory, PO Box 718-35, Mianyang 621907, Sichuan, China
› Author Affiliations
Further Information

Publication History

Received: 27 March 2015

Accepted after revision: 14 April 2015

Publication Date:
09 June 2015 (online)


This article is dedicated to our distinguished friend and colleague Professor K. Peter C. Vollhardt.

Abstract

Click chemistry involving copper-catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most useful and powerful methods to construct metallodendrimers. The design of such strategies includes the choice of the copper(I) catalyst source which is critical in the case of the click synthesis of dendrimers. The 1,2,3-triazolyl-containing dendrimers that are produced provide useful intradendritic ligands that are active in supramolecular recognition and catalysis. This account dedicated to K. Peter C. Vollhardt summarizes work conducted mainly in the authors’ Bordeaux laboratory.

1 Introduction

2 Click Copper Catalyzed Azide–Alkyne Cycloaddition Metallodendrimer Constructions

3 The Copper-Catalyzed Azide–Alkyne Cycloaddition Reactions in Dendrimers: Mind the Copper(I) Catalyst

4 Redox Recognition with Triazolylferrocenyl- and Triazolylbiferrocenyl-Terminated Dendrimers

5 Click Catalysis with Extremely Efficient Intradendritic Triazolyl–Copper(I) Complexes

6 Click Dendrimers as Stabilizers for Very Efficient Nanoparticle Catalysis of Cross-Coupling Carbon–Carbon Bond Formation and Redox Reactions

7 Click Dendrons and Dendrimers for Efficient Catalysis Using Magnetically Recoverable Catalysts

8 Conclusion and Prospects

 
  • References

  • 1 Diercks R, Armstrong JC, Boese R, Vollhardt KP. C. Angew. Chem. Int. Ed. Engl. 1986; 25: 268
  • 2 Boese Green JR, Mittendorf J, Mohler DL, Vollhardt KP. C. Angew. Chem. Int. Ed. Engl. 1992; 31: 1643
  • 3 Yu Y, Bond AD, Leonard PW, Lorenz UJ, Timofeeva TV, Vollhardt KP. C, Glenn DW, Yakovenko AA. Chem. Commun. (Cambridge) 2006; 24: 2572
  • 4 Modern Arene Chemistry . Astruc D. Wiley-VCH; Weinheim: 2002
  • 5 Diallo AK, Daran J.-C, Varret F, Ruiz J, Astruc D. Angew. Chem. Int. Ed. 2009; 48: 3141
  • 6 Diallo AK, Absalon C, Ruiz J, Astruc D. J. Am. Chem. Soc. 2011; 133: 629
  • 7 Astruc D. Nat. Chem. 2012; 4: 255
  • 8 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
  • 9 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
  • 10 Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
  • 11 Meldal M, Tornøe CW. Chem. Rev. 2008; 108: 2952
  • 12 Hein E, Fokin VV. Chem. Soc. Rev. 2010; 39: 1302
  • 13 Golas PL, Matyjaszewski K. Chem. Soc. Rev. 2010; 39: 1338
  • 14 Gil MV, Arévalo MJ, López O. Synthesis 2007; 1589
  • 15 Fournier D, Hoogenboom R, Schubert US. Chem. Soc. Rev. 2007; 36: 1369
  • 16 Sumerlin BS, Vogt AP. Macromolecules 2010; 43: 1
  • 17 Droumaguet B, Velonia K. Macromol. Rapid Commun. 2008; 29: 1073
  • 18 Struthers H, Mindt TL, Schibli R. Dalton Trans. 2010; 39: 675
  • 19 Binder WH, Sachsenhofer R. Macromol. Rapid Commun. 2007; 28: 15
  • 20 Mansfeld U, Pietsch C, Hoogenboom R, Becer CR, Schubert US. Polym. Chem. 2010; 1: 1560
  • 21 Binder WH, Zirbs R. ‘Click’ Chemistry in Macromolecular Synthesis, Encyclopedia of Polymer Science and Technology. Wiley; New York: 2009
  • 22 Kappe CO, van der Eycken E. Chem. Soc. Rev. 2010; 39: 1280
  • 23 Lutz JF, Zarafshani Z. Adv. Drug Delivery Rev. 2008; 60: 958
  • 24 Lutz JF, Borner HG. Prog. Polym. Sci. 2008; 33: 1
  • 25 Hua YR, Flood AH. Chem. Soc. Rev. 2010; 39: 1262
  • 26 Mullen DG, McNerny DQ, Desai A, Cheng X, DiMaggio SC, Kotlyar A, Zhong Y, Qin S, Kelly CV, Thomas TP, Majoros I, Orr BG, Baker JR, Holl MM. B. Bioconjugate Chem. 2011; 22: 679
  • 27 Aromi G, Barrios LA, Roubeau O, Gamez P. Coord. Chem. Rev. 2011; 255: 485
  • 28 Marsden HR, Kros A. Macromol. Biosci. 2009; 9: 939
  • 29 Kepe K, Krieg A, Becer CR, Schubert US. Chem. Soc. Rev. 2012; 41: 176
  • 30 Schulze B, Schubert US. Chem. Soc. Rev. 2014; 43: 2522
  • 31 Wong C.-H, Zimmerman SC. Chem. Commun. 2013; 49: 1679
  • 32 Tasdelen MA, Yagci Y. Angew. Chem. Int. Ed. 2013; 52: 5930
  • 33 Xi WX, Scott TF, Kloxin CJ, Bowman CN. Adv Funct. Mater. 2014; 24: 2572
  • 34 Wu P, Feldman AK, Nugent AK, Hawker CJ, Scheel A, Voit B, Pyun J, Fréchet JM. J, Sharpless KB, Fokin VV. Angew. Chem. Int. Ed. 2004; 43: 3928
  • 35 Franc G, Kakkar A. Chem. Commun. (Cambridge) 2008; 5267
  • 36 Franc G, Kakkar A. Chem. Soc. Rev. 2010; 39: 1536
  • 37 Ornelas C, Ruiz J, Cloutet E, Alves S, Astruc D. Angew. Chem. Int. Ed. 2007; 46: 872
  • 38 Diallo AK, Ornelas C, Salmon L, Ruiz J, Astruc D. Angew. Chem. Int. Ed. 2007; 46: 8644
  • 39 Moulines F, Astruc D. Angew. Chem. Int. Ed. Engl. 1988; 27: 1347
  • 40 Moulines F, Djakovitch L, Boese R, Gloaguen B, Thiel W, Fillaut J.-L, Delville M.-H, Astruc D. Angew. Chem. Int. Ed. Engl. 1993; 32: 1075
  • 41 Catheline D, Astruc D. J. Organomet. Chem. 1984; 272: 417
  • 42 Newkome GR, Yao ZQ, Baker GR, Gupta VK. J. Org. Chem. 1985; 50: 2003
  • 43 Newkome GR, Scheiner C. Chem. Rev. 2010; 110: 6338
  • 44 Sandler AC, Ruiz J, Astruc D. Organometallics 2010; 29: 5722
  • 45 Sartor V, Djakovitch L, Fillaut J.-L, Moulines F, Neveu F, Marvaud V, Guittard J, Blais J.-C, Astruc D. J. Am. Chem. Soc. 1999; 121: 2929
  • 46 Ruiz J, Lafuente G, Marcen S, Ornelas C, Lazare S, Cloutet E, Blais J.-C, Astruc D. J. Am. Chem. Soc. 2003; 125: 7250
  • 47 Rapakousiou A, Wang Y, Belin C, Pinaud N, Ruiz J, Astruc D. Inorg. Chem. 2013; 52: 6685
  • 48 Boisselier E, Diallo AK, Salmon L, Ornelas C, Ruiz J, Astruc D. J. Am. Chem. Soc. 2010; 132: 2729
  • 49 Wang Y, Salmon L, Ruiz J, Astruc D. Nat. Commun. 2014; 5: article number 3489
  • 50 Li N, Zhao P, Salmon L, Ruiz J, Zabawa M, Hosmane NS, Astruc D. Inorg. Chem. 2013; 52: 11146
  • 51 Camponovo J, Ruiz J, Cloutet E, Astruc D. Chem. Eur. J. 2009; 15: 2990
  • 52 Hamon J.-R, Astruc D, Michaud P. J. Am. Chem. Soc. 1981; 103: 758
  • 53 Madonik AM, Astruc D. J. Am. Chem. Soc. 1984; 106: 2437
  • 54 Djeda R, Rapakousiou A, Liang L, Guidolin N, Ruiz J, Astruc D. Angew. Chem. Int. Ed. 2010; 49: 8152
  • 55 Weyland T, Lapinte C, Frapper G, Calhorda MJ, Halet J.-F, Toupet L. Organometallics 1997; 16: 2024
  • 56 Paul F, Lapinte C. Coord. Chem. Rev. 1998; 178-180: 431
  • 57 Huisgen R. Angew. Chem. Int. Ed. Engl. 1963; 2: 565
  • 58 Li Z, Seo TS, Ju J. Tetrahedron Lett. 2004; 45: 3143
  • 59 Liang L, Ruiz J, Astruc D. Adv. Synth. Catal. 2011; 353: 3434
  • 60 Golas PL, Tsarevsky NV, Sumerlin BS, Matyjaszewski K. Macromolecules 2006; 39: 6451
  • 61 Candelon N, Lastécouères D, Diallo AK, Ruiz J, Astruc D, Vincent J.-M. Chem. Commun. (Cambridge) 2008; 741
  • 62 Zhao P, Grillaud M, Salmon L, Ruiz J, Astruc D. Adv. Synth. Catal. 2012; 354: 1001
  • 63 Astruc D, Liang L, Rapakousiou A, Ruiz J. Acc. Chem. Res. 2012; 45: 630
  • 64 Liang L, Astruc D. Coord. Chem. Rev. 2011; 255: 2933
  • 65 Valério C, Fillaut J.-L, Ruiz J, Guittard J, Blais J.-C, Astruc D. J. Am. Chem. Soc. 1997; 119: 2588
  • 66 Ornelas C, Salmon L, Ruiz J, Astruc D. Chem. Eur. J. 2008; 14: 50
  • 67 Rapakousiou A, Deraedt C, Irigoyen J, Wang Y, Pinaud N, Salmon L, Ruiz J, Moya S, Astruc D. Inorg. Chem. 2015; 54: 2284
  • 68 Diallo AK, Boisselier E, Liang L, Ruiz J, Astruc D. Chem. Eur. J. 2010; 16: 11832
  • 69 Deraedt C, Pinaud N, Astruc D. J. Am. Chem. Soc. 2014; 136: 12092
  • 70 Crooks RM, Zhao M, Sun L, Chechik V, Yeung LK. Acc. Chem. Res. 2001; 34: 181
  • 71 Scott RW. J, Wilson OM, Crooks RM. J. Phys. Chem. B 2005; 109: 692
  • 72 Lu F, Ruiz J, Astruc D. Tetrahedron Lett. 2004; 9443
  • 73 Toshima N, Yonezawa T. New J. Chem. 1998; 22: 1179
  • 74 Astruc D. Tetrahedron: Asymmetry. 2010; 21: 1041
  • 75 de Vries JG. A. Dalton Trans. 2006; 421
  • 76 Ornelas C, Ruiz J, Salmon L, Astruc D. Adv. Synth. Catal. 2008; 350: 837
  • 77 Deraedt C, Salmon L, Etienne L, Ruiz J, Astruc D. Chem. Commun. 2013; 49: 8169
  • 78 Deraedt C, Salmon L, Astruc D. Adv. Synth. Catal. 2014; 356: 2525
  • 79 Deraedt C, Astruc D. Acc. Chem. Res. 2014; 47: 494
  • 80 Ciganda R, Li N, Deraedt C, Gatard S, Zhao P, Salmon L, Hernández R, Ruiz J, Astruc D. Chem. Commun. 2014; 50: 10126
  • 81 Li N, Zhao P, Igartua ME, Rapakousiou A, Salmon L, Moya S, Ruiz J, Astruc D. Inorg. Chem. 2014; 53: 11802
  • 82 Zhao P, Feng X, Huang D, Yang G, Astruc D. Coord. Chem. Rev. 2015; 287: 114
  • 83 Wunder S, Lu Y, Albrecht M, Ballauff M. ACS Catal. 2011; 1: 908
  • 84 Herves P, Perez-Lorenzo M, Liz-Marzán LM, Dzubiella J, Lu Y, Ballauff M. Chem. Soc. Rev. 2012; 41: 5577
  • 85 Abu-Reziq R, Alper H, Wang D, Post ML. J. Am. Chem. Soc. 2006; 128: 5279
  • 86 Yu E, Yuzik-Klimova Kuchkina NV, Sorokina SA, Morgan DG, Boris B, Nikoshvili L, Lyubinova NA, Matveeva VG, Sulman EM, Stein BD, Mahmoud WE, Al-Ghamdi AA, Kostoupoulou A, Lappas A, Shifrina ZB, Bronstein LV. RSC Adv. 2014; 4: 23271
  • 87 Kuchkina NV, Morgan DG, Kostopoulou A, Lappas A, Brintakis K, Boris BS, Yuzik-Klimova EY, Stein BD, Svergun DI, Spilotros A, Sulman MG, Nikoshvili LZ, Sulman EM, Shifrina ZB, Bronstein LM. Chem. Mater. 2014; 26: 5654
  • 88 Wang D, Deraedt C, Salmon L, Labrugère C, Etienne L, Ruiz J, Astruc D. Chem. Eur. J. 2015; 21: 1508
  • 89 Deraedt C, Wang D, Salmon L, Etienne L, Labrugère C, Ruiz J, Astruc D. ChemCatChem 2015; 7: 303
  • 90 Wang D, Deraedt C, Salmon L, Labrugère C, Etienne L, Ruiz J, Astruc D. Chem. Eur. J. 2015; 21: 1
  • 91 Astruc D, Boisselier E, Ornelas C. Chem. Rev. 2010; 110: 1857
  • 92 Boisselier E, Astruc D. Chem. Soc. Rev. 2009; 38: 1759
  • 93 Jain RJ, Stylianopoulos T. Nat. Rev. Clin. Oncol. 2010; 7: 653