Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity

Org Biomol Chem. 2012 Oct 28;10(40):8059-63. doi: 10.1039/c2ob25215e.

Abstract

We describe here the determination of the alkylation rate of a set of organic superbases by iodomethane in DMF using a microfluidic continuous flow reactor. Surprisingly, log k(Alkylation) follows the inverse trend of pK(BH+) of the base. Mayr's equation allows a more quantitative approach. From a synthetic point of view, TMGN and BEMP are demonstrated to be the best choices.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Hydrocarbons, Iodinated / chemistry
  • Kinetics
  • Microfluidic Analytical Techniques*
  • Molecular Structure
  • Nitriles / chemistry*

Substances

  • Hydrocarbons, Iodinated
  • Nitriles
  • methyl iodide