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DOI: 10.1055/a-2356-8347
Harnessing the Reactivity of ortho-Alkynylaldehydes: Silver Triflate-Catalyzed Regioselective Synthesis of Phosphonylated Fluorescent Molecules
Gefördert durch: Science and Engineering Research Board CRG/2022/008887,IoE/2021/12/FRP![](https://www.thieme-connect.de/media/synthesis/0000AAM/lookinside/thumbnails/10.1055-a-2356-8347-1.jpg)
Abstract An efficient approach for the facile synthesis of phosphonylated 1,3-dihydrofuro[3,4-b]quinolines and dihydrofuro[3,4-b]pyridines is developed. Reaction proceeds by the formation of new C–P and C–O bonds affording Z-selective phosphonylated products at room temperature. Diphenylphosphine oxides and dialkylphosphites are explicitly incorporated into the carbonyl carbon of o-alkynyladehydes in good to excellent yields. The reaction exhibits mild reaction conditions, broad substrate scope, and the formation of three new bonds in the presence of a silver catalyst. The mechanistic studies revealed that the reaction proceeded via an ionic pathway in a 5-exo-dig manner to give Z-selective products which was validated by X-ray crystallographic studies. Photophysical studies of selected compounds revealed the emission maxima in the range of 455 nm.
Publikationsverlauf
Eingereicht: 22. Mai 2024
Angenommen nach Revision: 27. Juni 2024
Accepted Manuscript online:
28. Juni 2024
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