Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide

Handle URI:
http://hdl.handle.net/10754/599602
Title:
Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide
Authors:
Johansson, Johan R.; Lincoln, Per; Nordén, Bengt; Kann, Nina
Abstract:
An 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.
Citation:
Johansson 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.
Publisher:
American Chemical Society (ACS)
Journal:
The Journal of Organic Chemistry
Issue Date:
Apr-2011
DOI:
10.1021/jo200134a
PubMed ID:
21388208
Type:
Article
ISSN:
0022-3263; 1520-6904
Sponsors:
We 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).
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Full metadata record

DC FieldValue Language
dc.contributor.authorJohansson, Johan R.en
dc.contributor.authorLincoln, Peren
dc.contributor.authorNordén, Bengten
dc.contributor.authorKann, Ninaen
dc.date.accessioned2016-02-28T05:54:07Zen
dc.date.available2016-02-28T05:54:07Zen
dc.date.issued2011-04en
dc.identifier.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.en
dc.identifier.issn0022-3263en
dc.identifier.issn1520-6904en
dc.identifier.pmid21388208en
dc.identifier.doi10.1021/jo200134aen
dc.identifier.urihttp://hdl.handle.net/10754/599602en
dc.description.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.en
dc.description.sponsorshipWe 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).en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleSequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azideen
dc.typeArticleen
dc.identifier.journalThe Journal of Organic Chemistryen
dc.contributor.institutionChalmers University of Technology, Göteborg, Swedenen

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