Synthesis of homo-propargylic ethers: A domino ring opening/coupling reaction of oxiranes with terminal alkynes and aryl iodides

[Display omitted] •Domino ring opening/cross-coupling reaction of oxiranes.•Regioselective ring opening/cross-coupling reaction of oxiranes.•Chemoselective reaction of copper-acetylide with oxirane.•Catalytic synthesis of homo-propargylic ethers.•PEG-400 as environmental being solvent and ligand. A...

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Veröffentlicht in:Tetrahedron letters 2019-10, Vol.60 (44), p.151216, Article 151216
Hauptverfasser: Jahanshad, Milad, Manafi, Mohammadreza, Mahmoud Mousavi-Safavi, Seyed, Saied Homami, Seyed, Ghazanfarpour-Darjani, Majid
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Sprache:eng
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Zusammenfassung:[Display omitted] •Domino ring opening/cross-coupling reaction of oxiranes.•Regioselective ring opening/cross-coupling reaction of oxiranes.•Chemoselective reaction of copper-acetylide with oxirane.•Catalytic synthesis of homo-propargylic ethers.•PEG-400 as environmental being solvent and ligand. A domino ring opening/cross-coupling reaction of oxiranes with terminal alkynes and aryl iodides has been developed. This transformation serves as a protocol for the synthesis of homo-alkyne ether skeletons from the readily available starting materials. The success of the reaction has dependence on catalyst/ligand system of choice. The synthesis utility of the alkyne ether skeletons in formation of chromane skeleton has also been studied.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151216