Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength† †Electronic supplementary information (ESI) available: Detailed procedures and results for all reported experiments. CCDC 1568432. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc03866f
نویسندگان
چکیده
The benzodiselenazoles (BDS) introduced in this report fulfill, for the first time, all the prerequisites for noncovalent high-precision chalcogen-bonding catalysis in the focal point of conformationally immobilized s 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, s 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 s holes down to KD 1⁄4 11 mM in THF. Catalytic activities follow the same trend and culminate in rate enhancements for transfer hydrogenation of quinolines beyond 100 000.
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School of Chemistry and EaStCHEM, Un Andrews, Fife KY16 9ST, UK. E-mail: d.ph 463808; Tel: +44 (0)1334 467264 Institut de Génétique et de Biologie Molécu UMR 7104, Université de Strasbourg, Graffenstaden, France † Electronic supplementary information ( methods, synthesis and characterisation CCDC 1442418–1442421. For ESI and c electronic format see DOI: 10.1039/c6sc01 Cite this: Chem. Sci., 201...
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Department of Chemistry, Massachusetts I Avenue, Cambridge, MA, 02139-4307, USA. Department of Chemistry and Chemical Street, Cambridge, MA 02138-2902, USA. EDepartment of Chemistry, Queen's Univer Canada K7L 3N6. E-mail: [email protected] † Electronic supplementary information ( and crystallographic details. CCDC 14695 crystallographic data in CIF or o 10.1039/c6sc01754a Cite this: Chem. Sci., 20...
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