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

作者：Kim Woo Gyum; Kang Mi Eun; Lee Jae Bin; Jeon Min Ho; Lee Sungnin; Lee Jungha; Cho Bongseo; Cal Pedro M S D; Kang Sebyung; Kee Jung Min; Bernardes Goncalo J L; Rohde Jan Uwe; Choe Wonyoung; Hong Sung You^*

来源：Journal of the American Chemical Society, 2017, 139(35): 12121-12124.

DOI：10.1021/jacs.7b06338

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.

• 出版日期2017-9-6
• 单位河北医科大学