Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide
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AbstractAn experimentally simple sequential one-pot RuAAC reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields starting from an alkyl halide, sodium azide, and an alkyne, is reported. The organic azide is formed in situ by treating the primary alkyl halide with sodium azide in DMA under microwave heating. Subsequent addition of [RuClCp*(PPh 3) 2] and the alkyne yielded the desired cycloaddition product after further microwave irradiation. © 2011 American Chemical Society.
CitationJohansson JR, Lincoln P, Nordén B, Kann N (2011) Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide. J Org Chem 76: 2355–2359. Available: http://dx.doi.org/10.1021/jo200134a.
SponsorsWe thank Annika Langborg Weinmann at AstraZeneca R&D Molndal for kindly providing us with HRMS data of the products. We also thank Dr. Thomas Antonsson and Dr. Mikael Sellen for inspiring discussions. The Swedish NMR Centre is acknowledged for the use of high field NMR instruments. We thank Dr. Mate Erdelyi for advice concerning NOESY experiments. This work was funded by King Abdullah University of Science and Technology (KAUST).
PublisherAmerican Chemical Society (ACS)
JournalThe Journal of Organic Chemistry
CollectionsPublications Acknowledging KAUST Support
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