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

Johan R. Johansson; Per Lincoln; Bengt Nordén; Nina Kann

doi:10.1021/jo200134a

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

Johan R. Johansson, Per Lincoln, Bengt Nordén, Nina Kann

Research output: Contribution to journal › Article › peer-review

103 Scopus citations

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.

Original language	English (US)
Pages (from-to)	2355-2359
Number of pages	5
Journal	The Journal of Organic Chemistry
Volume	76
Issue number	7
DOIs	https://doi.org/10.1021/jo200134a
State	Published - Apr 2011
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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).
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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

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. {\textcopyright} 2011 American Chemical Society.",

author = "Johansson, {Johan R.} and Per Lincoln and Bengt Nord{\'e}n and Nina Kann",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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). This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2011",

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doi = "10.1021/jo200134a",

language = "English (US)",

volume = "76",

pages = "2355--2359",

journal = "The Journal of Organic Chemistry",

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T1 - Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide

AU - Johansson, Johan R.

AU - Lincoln, Per

AU - Nordén, Bengt

AU - Kann, Nina

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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). This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2011/4

Y1 - 2011/4

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/599602

UR - https://pubs.acs.org/doi/10.1021/jo200134a

UR - http://www.scopus.com/inward/record.url?scp=79953209022&partnerID=8YFLogxK

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SN - 0022-3263

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SP - 2355

EP - 2359

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 7

ER -

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

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