Copper-catalyzed reactions of alpha,beta-unsaturated N-tosylhydrazones with diaryliodonium salts to construct N-arylpyrazoles and diaryl sulfones

Herein, an economical copper-catalyzed reaction of alpha,beta-unsaturated N-tosylhydrazones with diaryliodonium salts to construct both N-arylpyrazoles and diaryl sulfones has been developed. Both the p-toluenesulfonyl anion and the 3-arylpyrazole intermediates were formed in situ from N-tosylhydrazones. Subsequently, the former reacted rapidly with diaryliodonium salts to give diaryl sulfones and aryl iodide intermediates, and the latter reacted with aryl iodide to give N-arylpyrazoles under copper-catalyzed conditions. Using unsymmetrical mesityl phenyliodonium salts as substrates, mesityl p-toluenesulfide was obtained as the major product. This reaction took full advantage of the "waste" part of substrates to form an extra diaryl sulfone.