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      Synthesis of a Crushed Fullerene C60H24 through Sixfold Palladium‐Catalyzed Arylation

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          Abstract

          The synthesis of a new C 3 v ‐symmetric crushed fullerene C 60H 24 ( 5) has been accomplished in three steps from truxene through sixfold palladium‐catalyzed intramolecular arylation of a syn‐trialkylated truxene precursor. Laser irradiation of 5 induces cyclodehydrogenation processes that result in the formation of C 60, as detected by LDI‐MS.

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          Groundwork for a rational synthesis of C60: cyclodehydrogenation of a C60H30 polyarene.

          M Boorum, Y Vasil'ev, T Drewello … (2001)
          A C60H30 polycyclic aromatic hydrocarbon (PAH) that incorporates all 60 carbon atoms and 75 of the 90 carbon-carbon bonds required to form the fullerene C60 has been synthesized in nine steps by conventional laboratory methods. Laser irradiation of this C60H30 PAH at 337 nanometers induces hydrogen loss and the formation of C60, as detected by mass spectrometry. A specifically labeled [13C3]C60H30 retains all three 13C atoms during the cage formation process. A structurally related C48H24 PAH that lacks the three peripheral benzene rings cannot be transformed into C60, whereas the next higher homolog, a C80H40 PAH, degrades to the C60H30 PAH, which then loses hydrogen to give [60]fullerene. These control experiments verify that the C60 is formed by a molecular transformation directly from the C60H30 PAH and not by fragmentation and recombination in the gas phase.
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            Palladium catalyzed arylation for the synthesis of polyarenes.

            Sergio Pascual, Paula de Mendoza, Antonio Echavarren (2007)
            We present the current understanding on the mechanism of palladium-catalyzed arylation, which involves a proton abstraction by the base. In addition, we present selected examples of the application of this reaction for the synthesis of large polyarenes to highlight the variety of catalysts and reaction conditions that are currently used.
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              Synthesis of a triaza analogue of crushed-fullerene by intramolecular palladium-catalyzed arylation.

              Berta Gómez-Lor, Antonio Echavarren (2004)
              Alkylation and intramolecular palladium-catalyzed arylation allows for the ready synthesis of C57H33N3 from symmetrical triindole, a triaza analogue of truxene.
              Article 0 comments Cited 11 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                Antonio M. Echavarren:
                ORCID: http://orcid.org/0000-0001-6808-3007
                aechavarren@iciq.es , http://www.iciq.org/research/research_group/prof‐antonio‐m‐echavarren/
                Journal
                Journal ID (nlm-ta): European J Org Chem
                Journal ID (iso-abbrev): European J Org Chem
                Journal ID (doi): 10.1002/(ISSN)1099-0690
                Journal ID (publisher-id): EJOC
                Title: European Journal of Organic Chemistry
                Publisher: John Wiley and Sons Inc. (Hoboken )
                ISSN (Print): 1434-193X
                Publication date (Electronic): 02 May 2016
                Publication date (Print): July 2016
                Volume: 2016
                Issue: 19 ( doiID: 10.1002/ejoc.v2016.19 )
                Pages: 3171-3176
                Affiliations
                [ 1 ] Institute of Chemical Research of Catalonia (ICIQ)Barcelona Institute of Science and Technology Av. Països Catalans 16 43007 TarragonaSpain
                [ 2 ] Departament de Química Orgànica i AnalíticaUniversitat Rovira i Virgili C/ Marcel·lí Domingo s/n 43007 TarragonaSpain
                Author notes
                [*] [* ] Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain

                E‐mail: aechavarren@ 123456iciq.es

                http://www.iciq.org/research/research_group/prof‐antonio‐m‐echavarren/

                [†]

                Current address: Medicinal Chemistry Department, Spanish National Cancer Research Centre (CNIO)C/ Melchor Fernández Almagro 3, 28029 Madrid, Spain

                Author information
                http://orcid.org/0000-0001-6808-3007
                Article
                Publisher ID: EJOC201600311
                DOI: 10.1002/ejoc.201600311
                PMC ID: 5053240
                SO-VID: 60add7a0-4e1f-4f42-a806-83e6906d98b2
                Copyright © © 2016 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA.
                License:

                This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.

                History
                Date received : 14 March 2016
                Page count
                Figures: 8, Tables: 0, Pages: 6, Words: 0
                Funding
                Funded by: European Research Council (ERC)
                Award ID: Advanced Grant No. 321066
                Categories
                Subject: Full Paper
                Subject: Full Papers
                Subject: Fullerenes
                Custom metadata
                source-schema-version-number 2.0
                component-id ejoc201600311
                cover-date July 2016
                details-of-publishers-convertor Converter:WILEY_ML3GV2_TO_NLMPMC version:4.9.4 mode:remove_FC converted:06.10.2016

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: fullerenes,truxene,palladium,arylation,mass spectrometry
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: fullerenes, truxene, palladium, arylation, mass spectrometry

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