Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

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

Nickel-Catalyzed Azide–Alkyne Cycloaddition To Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
Gonçalo J. L. Bernardes, Woo Gyum Kim, Mi Eun Kang, Sebyung Kang, Jae Bin Lee, Jan-Uwe Rohde, Pedro M. S. D. Cal, Sung You Hong, Jungha Lee, Bongseo Choi, Sungmin Lee, Min Ho Jeon, Wonyoung Choe, Jung-Min Kee
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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06338

DOI: 10.1021/jacs.7b06338

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