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Synthesis Of N-Sulfonyl- And N-Acylpyrroles Via A Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

Weiqiang Chen, Yin-Lin Zhang, Hui-Jing Li, Xiang Nan, Ying Liu, Yan-Chao Wu

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N-Sulfonyl- and N-acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf)2 and CuBr2, the reaction afforded N-sulfonyl- and N-acylpyrroles, respectively, in one pot. Under an oxygen atmosphere, the reaction went smoothly without the need of hydroperoxide oxidants. This protocol possesses many advantages, such as using a nonhazardous oxidant and readily available starting materials, operating in one pot, and showing a broad substrate scope.