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Issue 12, 2017
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Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

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Abstract

The benzodiselenazoles (BDS) introduced in this report fulfill, for the first time, all the prerequisites for non-covalent high-precision chalcogen-bonding catalysis in the focal point of conformationally immobilized σ holes on strong selenium donors in a neutral scaffold. Rational bite-angle adjustment to the long Se–C bonds was the key for BDS design. For the unprecedented BDS motif, synthesis of 12 analogs from o-xylene, crystal structure, σ hole variation strategies, optoelectronic properties, theoretical and experimental anion binding as well as catalytic activity are reported. Chloride binding increases with the depth of the σ holes down to KD = 11 μM in THF. Catalytic activities follow the same trend and culminate in rate enhancements for transfer hydrogenation of quinolines beyond 100 000.

Graphical abstract: Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

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Publication details

The article was received on 04 Sep 2017, accepted on 06 Oct 2017 and first published on 16 Oct 2017


Article type: Edge Article
DOI: 10.1039/C7SC03866F
Citation: Chem. Sci., 2017,8, 8164-8169
  • Open access: Creative Commons BY license
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    Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

    S. Benz, J. Mareda, C. Besnard, N. Sakai and S. Matile, Chem. Sci., 2017, 8, 8164
    DOI: 10.1039/C7SC03866F

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