Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
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- Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
- Kim, Woo Gyum; Kang, Mi Eun; Lee, Jae Bin; Jeon, Min Ho; Lee, Sungmin; Lee, Jungha; Choi, Bongseo; Cal, Pedro M. S. D.; Kang, Sebyung; Kee, Jung-Min; Bernardes, Gon&ccedil;alo J.L.; Rohde, Jan-Uwe; Choe, Wonyoung; Hong, Sung You
- Issue Date
- AMER CHEMICAL SOC
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.139, no.35, pp.12121 - 12124
- Transition-metal-catalyzed or metal-free azide-alkyne cycloadditions are versatile and indispensable synthetic 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 successfully applied to biomolecular reaction systems, the azide-alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a formidable challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a general synthetic 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 operationally simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are readily prepared via this nickel-catalyzed azide-alkyne cycloaddition.
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