DMPU-HF: Novel Nucleophilic Fluorinating Reagent

Introduction

An HF-based nucleophilic fluorination reagent is ideal for cost and atom economy. The most commonly used HF-based reagents are HF-organic base complexes like Olah’s reagent (pyridine-HF) and triethylamine-HF. However, these organic bases reduce the acidity of the system and may interfere with metal catalysts. For example, pyridine may bond strongly with many transition metals.

Our new HF-based reagent DMPU-HF (802794) overcomes these drawbacks. DMPU is non-basic, non-nucleophilic, and relatively weakly coordinating (toward cationic metal). Thus, DMPU-HF has high acidity and is less likely to interfere with metal catalysts. At the same time, DMPU is an excellent hydrogen-bonding acceptor that can form a stable complex with HF. Sigma-Aldrich is proud to offer the novel fluorinating reagent DMPU-HF (802794) in collaboration with the Hammond and Xu groups.



Advantages

  • Compatible with many metal catalysts1
  • High reactivity in acid-catalyzed reactions due to higher acidity compared to pyridine-HF and triethylamine-HF2
  • Bench-top stable

Representative Scheme

Special thanks to Professor Bo Xu and Professor GB Hammond for contributing this technology spotlight.

 

Materials

     
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