American Chemical Society
ja7b06338_si_001.pdf (5.27 MB)

Nickel-Catalyzed Azide–Alkyne Cycloaddition To Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water

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journal contribution
posted on 2017-08-16, 00:00 authored by Woo Gyum Kim, Mi Eun Kang, Jae Bin Lee, Min Ho Jeon, Sungmin Lee, Jungha Lee, Bongseo Choi, Pedro M. S. D. Cal, Sebyung Kang, Jung-Min Kee, Gonçalo J. L. Bernardes, Jan-Uwe Rohde, Wonyoung Choe, Sung You Hong
Transition-metal-catalyzed or metal-free azide–alkyne cycloadditions are methods to access 1,4- or 1,5-disubstituted 1,2,3-triazoles. Although the copper-catalyzed cycloaddition to access 1,4-disubstituted products has been applied to biomolecular reaction systems, the azide–alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are prepared via this cycloaddition.