Allyl-Assisted, Cu(I)-Catalyzed Azide–Alkyne Cycloaddition/Allylation Reaction: Assembly of the [1,2,3]Triazolo-4,5,6,7-tetrahydropyridine Core Structure

• Published in: Journal of organic chemistry Vol. 80; no. 21; pp. 11003 - 11012
• Main Authors: Deng, Xiaohu, Liang, Jimmy, Allison, Brett B, Dvorak, Curt, McAllister, Heather, Savall, Brad M, Mani, Neelakandha S
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.11.2015; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; ONE-POT REACTION; COPPER(I)-CATALYZED CYCLOADDITION; 1,2,3-TRIAZOLES; ACETYLIDES; TERMINAL ALKYNES; INTERMEDIATE; INTERNAL ALKYNES; CATALYST; ORGANIC AZIDES; ANTAGONISTS

We report a Cu­(I)-catalyzed azide–alkyne–allyl halide three-component reaction for a one-pot synthesis of 1,4-disubstituted 5-allyl-1,2,3-triazoles. The allyl moiety provides not only the electrophile but also a coordinating ligand to Cu, which is essential for the reaction to occur under mild cond...