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      Access to the Protoilludane Core by Gold-Catalyzed Allene-vinylcyclopropane Cycloisomerization

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          Abstract

          Gold(I)-catalyzed allene-vinylcyclopropane cycloisomerization leads to the tricyclic framework of the protoilludanes in a single step by a reaction that involves a cyclopropane ring expansion and a Prins cyclization.

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          Most cited references11

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          Versatile Photocatalytic Systems for H2 Generation in Water Based on an Efficient DuBois-Type Nickel Catalyst

          Manuela Groß, Anna Reynal, James R. Durrant … (2013)
          The generation of renewable H2 through an efficient photochemical route requires photoinduced electron transfer (ET) from a light harvester to an efficient electrocatalyst in water. Here, we report on a molecular H2 evolution catalyst (NiP) with a DuBois-type [Ni(P2 R′N2 R″)2]2+ core (P2 R′N2 R″ = bis(1,5-R′-diphospha-3,7-R″-diazacyclooctane), which contains an outer coordination sphere with phosphonic acid groups. The latter functionality allows for good solubility in water and immobilization on metal oxide semiconductors. Electrochemical studies confirm that NiP is a highly active electrocatalyst in aqueous electrolyte solution (overpotential of approximately 200 mV at pH 4.5 with a Faradaic yield of 85 ± 4%). Photocatalytic experiments and investigations on the ET kinetics were carried out in combination with a phosphonated Ru(II) tris(bipyridine) dye (RuP) in homogeneous and heterogeneous environments. Time-resolved luminescence and transient absorption spectroscopy studies confirmed that directed ET from RuP to NiP occurs efficiently in all systems on the nano- to microsecond time scale, through three distinct routes: reductive quenching of RuP in solution or on the surface of ZrO2 (“on particle” system) or oxidative quenching of RuP when the compounds were immobilized on TiO2 (“through particle” system). Our studies show that NiP can be used in a purely aqueous solution and on a semiconductor surface with a high degree of versatility. A high TOF of 460 ± 60 h–1 with a TON of 723 ± 171 for photocatalytic H2 generation with a molecular Ni catalyst in water and a photon-to-H2 quantum yield of approximately 10% were achieved for the homogeneous system.
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            Recent Methodologies That Exploit C-C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes.

            Gabriele Fumagalli, Steven Stanton, John Bower (2017)
            In this review, synthetic and mechanistic aspects of key methodologies that exploit C-C single-bond cleavage of strained ring systems are highlighted. The focus is on transition-metal-catalyzed processes that are triggered by C-C bond activation and β-carbon elimination, with the review concentrating on developments from mid-2009 to mid-2016.
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              Solid-State15N NMR Chemical Shift Anisotropy of Histidines:  Experimental and Theoretical Studies of Hydrogen Bonding†

              Yufeng Wei, Angel de Dios, Ann E McDermott (1999)
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                Author and article information

                Journal
                Journal ID (nlm-ta): Org Lett
                Journal ID (iso-abbrev): Org. Lett
                Journal ID (publisher-id): ol
                Journal ID (coden): orlef7
                Title: Organic Letters
                Publisher: American Chemical Society
                ISSN (Print): 1523-7060
                ISSN (Electronic): 1523-7052
                Publication date (Electronic): 20 August 2013
                Publication date (Print): 06 September 2013
                Volume: 15
                Issue: 17
                Pages: 4580-4583
                Affiliations
                [1]Institute of Chemical Research of Catalonia (ICIQ) , Av. Països Catalans 16, 43007 Tarragona, Spain
                Author notes
                [†]

                Additional address: Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, 43007 Tarragona, Spain.

                Article
                DOI: 10.1021/ol402188b
                PMC ID: 3774677
                PubMed ID: 23962171
                SO-VID: 2e64245e-d849-470f-a076-33f2026373e3
                Copyright © Copyright © 2013 American Chemical Society
                History
                Date received : 01 August 2013
                Categories
                Subject: Letter
                Custom metadata
                document-id-old-9 ol402188b
                document-id-new-14 ol-2013-02188b
                ccc-price

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry

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