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*

*School of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China, Email: lihuijingiccas.ac.cn, ycwuiccas.ac.cn

W. Chen, Y.-L. Zhang, H.-J. Li, X. Nan, Y. Liu, Y.-C. Wu, Synthesis, 2019, 51, 3651-3666.

DOI: 10.1055/s-0039-1690002

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Abstract

N-Sulfonyl- and N-acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines followed by in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. Under an oxygen atmosphere, the reaction worked smoothly without the need of hydroperoxide oxidants.

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Key Words

pyrroles, ring-closing methathesis, Grubbs catalyst, oxygen, oxydehydrogenation, tandem reactions

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ID: J66-Y2019