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Updated: Aug 24, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Base-promoted cascade β-F-elimination/electrocyclization/Diels-Alder/retro-Diels-Alder reaction: efficient access to
Xi-Shang Sun1, Xin-Yu Diao1, Xiu-Qin Dong1
1College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Wuhan University Wuhan Hubei 430072 P. R. China xiuqindong@whu.edu.cn cjwang@whu.edu.cn.
Abstract:
A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels-Alder/retro-Diels-Alder reaction of N-2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to high yields with excellent regio-/chemoselectivity control. Moreover, a reasonable reaction pathway was proposed, which was in accordance with the prepared reaction intermediate and control experiment results. The δ-carboline product could be easily converted into a new chiral Py-box-type ligand through simple synthetic transformations. This salient strategy featured the advantages of metal-free conditions, excellent regio-/chemoselectivity, good to high yields, and outstanding substrate tolerance. Importantly, the potential application of these fascinating δ-carboline derivative products is well demonstrated in the recognition of ferric ions.
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