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Click Metallodendrimers and Their Functions SYNLETT0936-52141437-2096 © Georg Thieme Verlag Stuttgart · New York 2015, 26, 1437–1449 1437 account Syn lett D. Astruc et al. Account Click Metallodendrimers and Their Functions Didier Astruc*a Roberto Cigandaa,b Christophe Deraedta Sylvain Gatarda Liyuan Lianga Na Lia Catia Ornelasa,c Amalia Rapakousioua Jaime Ruiza Dong Wanga Yanlan Wanga Pengxiang Zhaoa,d a ISM, UMR CNRS 5255, Université Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France [email protected] b Facultad de Química de San Sebastián, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain c Institute of Chemistry, University of Campinas, Campinas 13083-970, Sao Paulo, Brazil d Nano Chemistry Group, Science and Technology on Surface Physics and Chemistry Laboratory, PO Box 718-35, Mianyang 621907, Sichuan, China This article is dedicated to our distinguished friend and colleague Professor K. Peter C. Vollhardt. Received: 27.03.2015 butadiynylbenzenes,2 and even the so-called ‘impossible Accepted after revision: 14.04.2015 molecule’ hexaferrocenylbenzene.3 His reports have Published online: 09.06.2015 4 DOI: 10.1055/s-0034-1380699; Art ID: st-2015-b0222-a inspired the organic and organometallic communities, including ourselves, towards the synthesis of star-shaped Abstract Click chemistry involving copper-catalyzed azide–alkyne cy- organometallics such as hexa(ferrocenylethynyl)benzenes5,6 cloaddition (CuAAC) is one of the most useful and powerful methods to and many ferrocene-containing star-shape6 and dendritic construct metallodendrimers. The design of such strategies includes 7 the choice of the copper(I) catalyst source which is critical in the case of molecules. the click synthesis of dendrimers. The 1,2,3-triazolyl-containing den- The concept of click chemistry8–12 has introduced major drimers that are produced provide useful intradendritic ligands that are facile methods in synthetic chemistry, in particular cop- active in supramolecular recognition and catalysis. This account dedi- per(I)-catalyzed azide–alkyne cycloaddition (CuAAC) using cated to K. Peter C. Vollhardt summarizes work conducted mainly in the authors’ Bordeaux laboratory. terminal alkynes such as Vollhardt’s alkynyl-containing 2–5 1 Introduction molecules. This reaction has been applied to an enor- 2 Click Copper Catalyzed Azide–Alkyne Cycloaddition Metalloden- mous range of compounds from organic derivatives of bio- Downloaded by: Dot. Lib Information. Copyrighted material. drimer Constructions medical interest to macromolecules and nanomaterials.13–33 3 The Copper-Catalyzed Azide–Alkyne Cycloaddition Reactions in The first exploration of a convergent dendrimer synthesis Dendrimers: Mind the Copper(I) Catalyst 4 Redox Recognition with Triazolylferrocenyl- and Triazolylbiferro- and its extension to the syntheses of higher-generation cenyl-Terminated Dendrimers dendrimers was reported by the Sharpless and Fréchet 5 Click Catalysis with Extremely Efficient Intradendritic Triazolyl– groups in 2004,34 and the field of click dendrimer synthesis Copper(I) Complexes has been reviewed by Franc and Kakkar.35,36 Dendrimer 6 Click Dendrimers as Stabilizers for Very Efficient Nanoparticle Ca- synthesis using the CuAAC reaction is especially appropri- talysis of Cross-Coupling Carbon–Carbon Bond Formation and Redox Reactions ate because this reaction involves mild conditions for com- 7 Click Dendrons and Dendrimers for Efficient Catalysis Using Mag- pletion, and the copper(I)-catalyzed cycloaddition allows netically Recoverable Catalysts perfect 1,4-regioselectivity for 1,2,3-triazole (trz) forma- 8 Conclusion and Prospects tion. These conditions are essential for the clean construc- tion of dendrimers. Key words click chemistry, dendrimers, triazoles, metallocenes, catal- ysis, sensing In 2007, our group reported the first click synthesis of metallodendrimers (Scheme 1).37 Iterative click construc- tion of several generations was achieved, and the use of 1 Introduction these trz-metallodendrimers in redox sensing37 and cataly- sis38 was reported. Indeed, we believed that the CuAAC click The star chemist and lecturer, Peter Vollhardt, among reaction was not only an appropriate tool for the synthesis his spectacular synthetic achievements, is the father of of metal-containing dendrimers, but also a practical meth- star-shaped molecules such as hexaethynylbenzene,1 hexa- od to introduce useful trz ligands for the above functions. In © Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 1437–1449 1438 Syn lett D. Astruc et al. Account Biographical Sketches Didier Astruc studied in Rennes, complet- denne, and his research interests are in or- Jaime Ruiz studied with E. Roman in Santi- ing two theses working with R. Dabard be- ganometallic and carbohydrate chemistry. ago de Chile, completed his Ph.D. in or- fore doing postdoctoral studies at the ganometallic chemistry with Didier Astruc Massachusetts Institute of Technology Liyuan Liang completed her Ph.D. with in 1989, and did postdoctoral studies with (MIT) with R. R. Schrock. He became Profes- Didier Astruc in 2011 on dendritic nanore- A. H. Cowley at the University of Texas at sor of Chemistry in Bordeaux in 1983 and actors in catalysis and molecular recogni- Austin. After his habilitation, he became an did a sabbatical at the University of Califor- tion. She is now Associate Professor in engineer. His interests are in inorganic elec- nia (UC), Berkeley, with Peter Vollhardt in Chongqing. Her interests are in organic/ trochemistry, nanoparticles, and metallo- 1990–1991. He is a member of the Institut inorganic hybrid nanomaterials. dendrimers. Universtaire de France and of several acade- Na Li studied with S. Yan in Lanzhou and mies. Dong Wang studied organic chemistry then joined Didier Astruc’s group, where with B. Chen in Lanzhou where he received Roberto Ciganda completed his Ph.D. she completed her Ph.D. in 2014 on gold a doctoral degree. He completed a second with M. A. Garralda Hualde in 2013 at the nanoparticle sensors. She is now doing Ph.D. with Professor Didier Astruc in 2014 Downloaded by: Dot. Lib Information. Copyrighted material. University of San Sebastian before working postdoctoral studies on dendrimers with A. on magnetic and dendritic nanocatalysis there with R. Hernandez. He is now doing Kakkar at McGill University, Montreal. and is presently working as a postdoctoral postdoctoral studies with Didier Astruc on researcher with D. Song in Toronto. Catia Ornelas studied in Madeira with J. catalysis with metallodendrimers and Rodrigues, completed her Ph.D. with Didier nanoparticles. Yanlan Wang studied with W. Zhang in Astruc on nanochemistry in 2007, and did Shanghai and completed her Ph.D. with Christophe Deraedt completed his Ph.D. successive postdoctoral studies with M. Didier Astruc in 2013 on metallodendrimer with Didier Astruc on catalysis in dendritic Weck at New York University, J. M. J. Fréchet chemistry and electronics. She is now con- nanoreactors in 2014 and is now doing at UC Berkeley, and A. Moore at Arizona ducting postdoctoral studies with M. postdoctoral studies in Tokyo with M. Fujita State University. She is Assistant Professor Malacria in Gif-sur-Yvette. on nanoreceptors. at UNICAMP, Sao Paulo, working on nano- materials in biomedicine. Pengxiang Zhao studied in Chengdu with Sylvain Gatard obtained his Ph.D. in 2002 W. Chen and completed his Ph.D. with with Didier Astruc and did postdoctoral Amalia Rapakousiou conducted under- Didier Astruc in 2012 on functional gold studies with R. Neumann at the Weizmann graduate studies in Athens and Bordeaux nanoparticle vectors for docetaxel delivery. Institute and then O. V. Ozerov at Brandeis and completed her Ph.D. with Didier Astruc He is an independent researcher in University. He is now Assistant Professor on redox nanomaterials in 2014. She is now Mianyang and his is interests are in gold at the University of Reims Champagne-Ar- doing postdoctoral studies in Tokyo with H. nanoparticle vectors, sensors, and cata- Nishihara on inorganic nanodevices. lysts. © Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 1437–1449 1439 Syn lett D. Astruc et al. Account the present account, we summarize our work and results 2 Click Copper Catalyzed Azide–Alkyne Cy- on the click syntheses of metallodendrimers, the products’ cloaddition Metallodendrimer Constructions resulting supramolecular properties, and the functions and applications of the trz groups in click metallodendrimers. The CpFe+-induced [CpFe+ = η5-cyclopentadienyl- iron(1+)] nona-allylation of mesitylene using allyl bromide and potassium hydroxide in tetrahydrofuran or 1,2-dime- Downloaded by: Dot. Lib Information. Copyrighted material. Scheme 1 Click (CuAAC) synthesis of a zeroth-generation (G0) ferrocenyl-terminated dendrimer (top); the dendritic construction of the larger den- drimers (G1–G4) then proceeds according to 1 → 3 connectivity (vide infra, Scheme 2) and the 81-ferrocenyl dendrimer (G2) is represented (bottom) © Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 1437–1449 1440 Syn lett D. Astruc et al. Account thoxyethane under ambient conditions39,40 followed by visi- Further hydrosilylation of 1 with (chloromethyl)di- ble-light photodecomplexation41 in the presence of mesity- methylsilane using the Karstedt catalyst45 followed by azi- lene provides a remarkable access to useful nona-allyl dation with sodium azide provides clickable dendritic arene-centered dendritic core 1.39,40 This reaction involving nona-azido precursor 2 (Scheme 3).37
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