Accelerated Reactivity Mechanism and Interpretable Machine Learning Model of N-Sulfonylimines toward Fast Multicomponent Reactions

Org Lett. 2020 Nov 6;22(21):8480-8486. doi: 10.1021/acs.orglett.0c03083. Epub 2020 Oct 19.

Abstract

We introduce chemical reactivity flowcharts to help chemists interpret reaction outcomes using statistically robust machine learning models trained on a small number of reactions. We developed fast N-sulfonylimine multicomponent reactions for understanding reactivity and to generate training data. Accelerated reactivity mechanisms were investigated using density functional theory. Intuitive chemical features learned by the model accurately predicted heterogeneous reactivity of N-sulfonylimine with different carboxylic acids. Validation of the predictions shows that reaction outcome interpretation is useful for human chemists.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemistry
  • Imines / chemistry*
  • Kinetics
  • Machine Learning*
  • Models, Chemical*

Substances

  • Carboxylic Acids
  • Imines