AI Article Synopsis
- The study presents a method using palladium as a catalyst to create 4-amidyl-2-aminopyrroles through a cyclization process involving alkynylimines and double isocyanides.
- The mechanism reveals a crucial four-membered ring intermediate and features several steps including cycloaddition and rearomatization.
- Notably, one of the synthesized dipyrrole derivatives shows significant fluorescence changes when exposed to fluoride ions, suggesting its potential use in optoelectronic applications.
Article Abstract
In this work, a palladium-catalyzed cyclization of alkynylimines and double isocyanides is described. This facile procedure is efficient for synthesizing various 4-amidyl-2-aminopyrroles. Mechanism investigation indicates that a four-membered ring-fused pyrrole species is a key intermediate and the reaction involves [4 + 1] cycloaddition, protonation, nucleophilic addition, 1,4-addition of isocyanide, and rearomatization. Interestingly, the linear dipyrrole derivative is found to be an appropriate fluoride ion probe with a remarkable emission change, which could serve as a potential candidate for optoelectronic conjugated materials.
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| http://dx.doi.org/10.1021/acs.joc.0c00323 | DOI Listing |
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Palladium-Catalyzed Cycloaddition of Alkynylimines, Double Isocyanides, and HO/KOAc.
J Org Chem
May 2020
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China.
Article Synopsis
- The study presents a method using palladium as a catalyst to create 4-amidyl-2-aminopyrroles through a cyclization process involving alkynylimines and double isocyanides.
- The mechanism reveals a crucial four-membered ring intermediate and features several steps including cycloaddition and rearomatization.
- Notably, one of the synthesized dipyrrole derivatives shows significant fluorescence changes when exposed to fluoride ions, suggesting its potential use in optoelectronic applications.
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