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Synthesis 2020; 52(05): 744-754
DOI: 10.1055/s-0039-1691506
DOI: 10.1055/s-0039-1691506
paper
A Copper(I)-Mediated Tandem Three-Component Synthesis of 5-Allyl-1,2,3-triazoles
This research was supported by the National Research Foundation of Korea (NRF-2018R1A5A2025286 and NRF-2017M3A9F5029066) with grants funded by the Government of South Korea.Further Information
Publication History
Received: 18 September 2019
Accepted after revision: 13 November 2019
Publication Date:
25 November 2019 (online)
‡ These authors contributed equally to this work.
Abstract
A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH2 is developed. The reactions proceed smoothly at room temperature to afford 5-allyl-1,2,3-triazoles, which can be further converted into 1,2,3-triazole-fused tricyclic scaffolds. This method features an efficient one-pot cascade route using commercial alkynes and affords the corresponding 5-allyl-1,2,3-triazoles with high yields and good selectivity under mild reaction conditions.
Key words
1,2,3-triazoles - multicomponent reactions - one-pot reactions - click reactions - copper catalystSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691506.
- Supporting Information
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For the synthesis of 5-allyl-1,2,3-triazoles, see:
For recent multicomponent CuAAC reactions, see: