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J Org Chem. 2018 Apr 20;83(8):4805-4811. doi: 10.1021/acs.joc.8b00022. Epub 2018 Apr 5.

Copper(I)-Catalyzed Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Azidoformates and Aryl Terminal Alkynes.

Author information

1
Department of Bionanotechnology , Hanyang University , Sangnok-gu Hanyang Daehak-ro 55 , Ansan , Gyeonggi-do 15588 , Republic of Korea.
2
Center for Neuro-Medicine , Korea Institute of Science and Technology (KIST) , Seongbuk-gu Hwarangro 14-gil 5 , Seoul 136-791 , Republic of Korea.
3
Department of Applied Chemistry , Hanyang University , Sangnok-gu Hanyang Daehak-ro 55 , Ansan , Gyeonggi-do , 15588 , Republic of Korea.

Abstract

The copper(I)-catalyzed azide-alkyne cycloaddition reaction has been extensively studied and widely applied in organic synthesis. However, the formation of 1,2,3-triazoles with electron-deficient azide has been a challenging problem. In this report, we have demonstrated the formation of regioselective 1,4-disubstituted 1,2,3-triazoles from various types of aryl terminal alkynes and azidoformates, which are electron-deficient azides, using a commercialized [Cu(CH3CN)4]PF6 copper(I) catalyst under mild conditions.

PMID:
29600859
DOI:
10.1021/acs.joc.8b00022

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