Visible-Light Photoredox-Catalyzed Radical Fluoromethoxylation of Olefins
S2 Table of Contents 1. General remarks.............................................................................................................................. 3 2. Starting materials ............................................................................................................................ 4 3. Synthesis of (2,4-dimethylphenyl)(fluoromethyl)(phenyl)sulfonium tetrafluoroborate (I) ........... 5 4. General procedure for the synthesis of N-fluoromethoxypyridinium salts.................................... 6 5. General procedure for the synthesis of N-fluoromethoxybenzotriazolium salts ........................... 8 6. Multigram scale synthesis of 1-(fluoromethoxy)-3-methyl-1H-benzo[d][1,2,3]triazol-3-ium trifluoromethanesulfonate (2aa) .......................................................................................................... 11 7. Cyclic voltammetry measurements .............................................................................................. 12 8. Differential scanning calorimetry and Thermogravimetric analysis of reagents (2a) and (2aa) .. 18 9. X-ray crystal structures of reagents 1d, 2aa and 2ad ................................................................... 19 Structure of 1d ...................................................................................................................................... 19 Structure of 2aa .................................................................................................................................... 20 Structure of 2ad .................................................................................................................................... 21 10. Optimization of the reaction conditions ................................................................................... 23 10.1 Amino-fluoromethoxylation of alkenes ................................................................................ 23 10.2 α-Monofluoromethoxylation of ketones .............................................................................. 26 11. Mechanistic Studies .................................................................................................................. 28 12. General procedure for amino-fluoromethoxylation of alkenes ............................................... 33 13. Characterization data of amino-fluoromethoxylated products................................................ 35 14. X-ray crystal structure of products 4p and 4r ........................................................................... 44 Structure of product 4p ........................................................................................................................ 44 Structure of product 4r ......................................................................................................................... 46 15. General procedure for α-fluoromethoxylation of ketones ....................................................... 48 16. Characterization data of α-fluoromethoxylated ketones ......................................................... 49 17. Further applications .................................................................................................................. 53 18. Scale up experiments ................................................................................................................ 57 19. References ................................................................................................................................ 59 20. Copies of 1H, 19F and 13C Spectra ............................................................................................... 60
Pieteikuma datums
06.04.2023.
Atslēgas vārdi
Visible-Light Photoredox-Catalyzed Radical Fluoromethoxylation of Olefins
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https://onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fadsc.202300130&file=adsc202300130-sup-0001-misc_information.pdf
