Copper-catalyzed sulfonylation of N-tosylhydrazones followed by a one-pot C-N bond formation

A new methodology to synthesize sulfonyl-N-phenylaniline derivatives via the trapping of bromo-sulfone derivatives generated from N-tosylhydrazones (NTHs) with amines is described. The reaction proved successful for a wide range of NTHs and amines and tolerated various functional groups on either coupling partner (35 examples). The mechanism was studied, and we showed that the sulfone formation does not follow a radical pathway.

Automated summary

A new methodology for synthesizing sulfonyl-N-phenylaniline derivatives by trapping bromo-sulfone derivatives with amines generated from N-tosylhydrazones (NTHs) was described. The reaction was successful for a wide range of NTHs and amines, and tolerated various functional groups on both coupling partners (35 examples). Mechanistic studies showed that sulfone formation did not proceed through a radical pathway.