1‑(N‑Acylamino)alkyl Sulfones from N‑Acyl-α-amino Acids or N‑Alkylamides

A variety of N-(1-methoxyalkyl)­amides or carbamates react readily with sodium aryl sulfinates in the presence of triphenylphosphonium tetrafluoroborate or bromide in CHCl₃ under mild conditions to give 1-(N-acylamino)­alkyl sulfones in good yields. A combination of this reaction with the recently described electrochemical decarboxylative α-methoxylation of N-acyl-α-amino acids to give N-(1-methoxyalkyl)­amides in the presence of 3-(1-piperidino)­propyl-functionalized silica gel (SiO₂–Pip) enables an effective two-pot transformation of N-acyl-α-amino acids to 1-(N-acylamino)­alkyl sulfones. Alternatively, N-(1-methoxyalkyl)­amides can be obtained by electrochemical α-methoxylation of either N-alkylamides, lactams, or N-alkylcarbamates.