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Synthesis 2019; 51(19): 3651-3666
DOI: 10.1055/s-0039-1690002
DOI: 10.1055/s-0039-1690002
paper
Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction
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.
Key words
N-substituted pyrroles - ring-closing methathesis - Grubbs catalyst - Oxydehydrogenation - tandem reactionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690002.
- Supporting Information
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For the synthesis of pyrroles without the use of RCM strategy, see:
For pyrroles as pharmaceuticals, see:
For pyrrole-type biologically active natural products, see: