A Mild Multi-Component Reaction for the Synthesis of 4,5-Disubstituted 1H-1,2,3-Triazoles from Phosphonium Salts, Aldehydes, and Sodium Azide

Guang-Long Wu, Qin-Pei Wu*

*School of Chemistry and Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, China, Email: qpwubit.edu.cn

G.-L. Wu, Q.-P. Wu, Synthesis, 2018, 50, 2768-2774.

DOI: 10.1055/s-0037-1609720

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Abstract

A mild and metal-free multi-component reaction enables the synthesis of 4,5-disubstituted 1H-1,2,3-triazoles from phosphonium salts, aldehydes, and sodium azide. An organocatalyzed coupling of the formyl group with the phosphonium group provides an olefinic phosphonium salt as key intermediate, that undergoes [3+2] cycloaddition with the azide.

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Key Words

phosphonium salts, triazoles, organocatalysis, multicomponent reactions, cycloadditions

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ID: J66-Y2018