Synthesis 2019; 51(19): 3651-3666
DOI: 10.1055/s-0039-1690002
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

Weiqiang Chen
a   School of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China
,
Yin-Lin Zhang
a   School of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China
,
Hui-Jing Li
a   School of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China
b   Weihai Institute of Marine Biomedical Industrial Technology, Wendeng District, Weihai 264400, P. R. of China   Email: lihuijing@iccas.ac.cn   Email: ycwu@iccas.ac.cn
,
Xiang Nan
a   School of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China
,
Ying Liu
a   School of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China
,
Yan-Chao Wu
a   School of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China
b   Weihai Institute of Marine Biomedical Industrial Technology, Wendeng District, Weihai 264400, P. R. of China   Email: lihuijing@iccas.ac.cn   Email: ycwu@iccas.ac.cn
› Author Affiliations
This work was supported by the Natural Science Foundation of Shandong Province (ZR2019MB009), the Fundamental Research Funds for the Central Universities (HIT.NSRIF.201701), the Natural Science Foundation of China (21672046, 21372054), and funding from the Huancui District of Weihai City.
Further Information

Publication History

Received: 07 June 2019

Accepted after revision: 26 June 2019

Publication Date:
15 July 2019 (online)


Abstract

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.

Supporting Information

 
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