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Has files: Yes × search.filters.applied.f.series: Angewandte Chemie : a journal of the Gesellschaft Deutscher Chemiker : International edition 59 (2020), Nr. 42 ×

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    Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst
    (Weinheim : Wiley-VCH, 2020) Ryabchuk, Pavel; Leischner, Thomas; Kreyenschulte, Carsten; Spannenberg, Anke; Junge, Kathrin; Beller, Matthias
    A bifunctional 3d-metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr-C@SiO2-L is obtained by pyrolysis of a cobalt-impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson-Kass condensation provides >40 pyrroles in good to high yields using dihydrogen, formic acid, or a CO/H2O mixture (WGSR conditions) as reductant. In addition to the favorable step economy, this straightforward domino process does not require any solvents or external co-catalysts. The general synthetic utility of this methodology was demonstrated on a variety of functionalized substrates including the preparation of biologically active and pharmaceutically relevant compounds, for example, (+)-Isamoltane. © 2020 The Authors. Published by Wiley-VCH GmbH
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    Proton-Gated Ring-Closure of a Negative Photochromic Azulene- Based Diarylethene
    (Weinheim : Wiley-VCH, 2020) Hou, Ian Cheng-Yi; Berger, Fabian; Narita, Akimitsu; Müllen, Klaus; Hecht, Stefan
    Proton-responsive photochromic molecules are attractive for their ability to react on non-invasive rapid optical stimuli and the importance of protonation/deprotonation processes in various fields. Conventionally, their acidic/basic sites are on hetero-atoms, which are orthogonal to the photo-active π-center. Here, we incorporate azulene, an acid-sensitive pure hydrocarbon, into the skeleton of a diarylethene-type photoswitch. The latter exhibits a novel proton-gated negative photochromic ring-closure and its optical response upon protonation in both open and closed forms is much more pronounced than those of diarylethene photoswitches with hetero-atom based acidic/basic moieties. The unique behavior of the new photoswitch can be attributed to direct protonation on its π-system, supported by 1H NMR and theoretical calculations. Our results demonstrate the great potential of integrating non-alternant hydrocarbons into photochromic systems for the development of multi-responsive molecular switches. © 2020 The Authors. Published by Wiley-VCH GmbH