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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, Gonç,alo J. L.,Rohde, Jan-Uwe,Choe, Wonyoun American Chemical Society 2017 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.139 No.35
<P>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.</P>