Metal‐Catalyzed One‐Pot Synthesis of Tetrazines Directly from Aliphatic Nitriles and Hydrazine

2012/04/18 by Jun Yang, Mark R. Karver, Weilong Li +2 · 4 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · #Click Chemistry and Applications #Chemical Synthesis and Analysis #Nanomaterials for catalytic reactions

paper · doi:10.1002/anie.201201117

openalex publication_date 2012/04/18 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

Paving the way: The lack of convenient synthetic methods is a significant roadblock to the broader use of 1,2,4,5-tetrazines in bioorthogonal chemistry and functional materials. Lewis acid metal catalysts—most notably divalent nickel and zinc salts—are described to catalyze the one-pot synthesis of 1,2,4,5-tetrazines directly from aliphatic nitriles (see scheme).

Citations

• Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell Imaging
• Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity

Cited by

• In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live‐Cell Imaging Probes
• Live‐Cell Imaging of Cyclopropene Tags with Fluorogenic Tetrazine Cycloadditions
• A Bioorthogonal Near-Infrared Fluorogenic Probe for mRNA Detection
• Neal Devaraj [wikipedia]

Related

• Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity
• s-Tetrazine: Robust and Green Photoorganocatalyst for Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones
• One-Pot Strategic Synthesis of 1,3,5-Pyrazoline Derivatives using NiFe2O4.Cu(OH)2 Magnetic Nanocomposite as Heterogeneous Catalyst and their Theoretical Studies as Antifungal Agents
• Click chemistry reactions in medicinal chemistry: Applications of the 1,3‐dipolar cycloaddition between azides and alkynes
• Electrosynthesis of nitriles from primary alcohols and ammonia on Ni catalysts