Flow Alkylation of Thiols, Phenols, and Amines Using a Heterogenous Base in a Packed-Bed Reactor

Rapid alkylations of thiols are performed in a packed-bed flow reactor where potassium carbonate acts as a heterogeneous base in anhydrous solvents at ambient temperature. The reaction also has a high efficiency as the removal of the solvent is the only work up required to isolate the product. The products can be used in a subsequent oxidation which was performed sequentially in semibatch mode. The alkylations of phenol and benzyl amine have been demonstrated on an array of bases, but higher temperatures and longer reaction times are required than with thiols.