Science Advances

Supplementary Materials

This PDF file includes:

  • General methods
  • Optimization of reaction parameters
  • General procedures
  • Resin capacity in varying solvents
  • PMI calculations
  • Mechanistic studies
  • Spectroscopic data
  • 1H and 13C NMR spectra
  • Chiral HPLC traces for enantiopurity measurements
  • 1H and 13C NMR spectra for enantiopurity measurements
  • table S1. Solvent screen for general amidation.
  • table S2. Screening of borate reagents in amino acid amidation.
  • table S3. Varying time, catalyst loading, and equivalents of amine.
  • table S4. Varying concentration.
  • table S5. Reaction troubleshooting.
  • table S6. Solvent screen for resin workup.
  • table S7. Raw data for PMI calculations for amidation product 10.
  • table S8. PMI calculations for amidation product 10.
  • table S9. Raw data for PMI calculations.
  • table S10. PMI calculations.
  • table S11. Raw data for determination of order in catalyst.
  • table S12. Raw data for determination of order in catalyst.
  • table S13. Raw data for determination of order in catalyst.
  • table S14. Raw data for determination of order in amine.
  • table S15. Raw data for determination of order in amine.
  • table S16. Raw data for determination of order in amine.
  • table S17. Raw data for determination of order in acid.
  • table S18. Raw data for determination of order in acid.
  • table S19. Raw data for determination of order in acid.
  • table S20. Raw data for determination of order in acid.
  • table S21. Raw data for determination of order in acid.
  • fig. S1. Representative example of a Dean-Stark reaction setup.
  • fig. S2. Representative examples of a Dean-Stark setup with adaptor for the addition of ketone/aldehyde.
  • fig. S3. Representative example of a resin workup.
  • fig. S4. Green metrics for catalytic amidation protocols.
  • fig. S5. 19F NMR spectra of the crude reaction mixture (top) and the Dean-Stark (bottom) with fluorobenzene as an internal standard.
  • fig. S6. 11B NMR spectra of B(OCH2CF3)3 (top) and reaction mixture (bottom two) at 4- and 24-hour intervals.
  • References (47–66)

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