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Professor GB Hammond, University of Louisville & Professor Bo Xu, Donghua University, China

Research Interests The Hammond-Xu Research Group

Nucleophilic Fluorination: The selective substitution of hydrogen by fluorine constitutes a key strategy in drug discovery. Despite its importance in medicinal chemistry and in agrochemicals, the chemical space of fluorine is limited to mostly aromatic fluorine containing building blocks. Fluoroaliphatic or fluoroheterocycles are prepared on a case-by-case basis using boutique-type reactions that may employ either expensive, corrosive, and toxic fluorinated reagents, or in other cases fluorinated reagents that can only be used at low temperatures and inert atmospheres due to their limited thermal- and air/water stability, whereas yet in other applications, fluorinated reagents pose environmental problems.

Because most, if not all, fluorinating reagents are made from hydrogen fluoride (HF), an HF-based fluorinating reagent would be an ideal reagent in terms of cost and atom economy, but HF itself is a hazardous gas at room temperature and is very difficult to handle without special equipment. Recently, we developed a new HF-based reagent—DMPU-HF (DMPU = 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone), and demonstrated that it was a stable and efficient nucleophilic fluorination reagent in the gold-catalyzed hydrofluorination of alkynes,1 in the fluoro-Prins cyclization,2 and in the synthesis of -fluoroamines from aziridines.3 HF-DMPU is compatible with many metal catalysts, and is highly reactive, yet a selective reagent, in acid-catalyzed reactions.


Stable Hydrogen Fluoride (HF) Complex for Nucleophilic Fluorination DMPU-HF

• Alternative Liquid for HF Gas
• Bench-top Stable
• Less Interference with Metal Catalysts

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Technical Applications

Gold Complex Catalyzed Fluorination of Alkynes

Fluoro-Prins Reaction

Fluorination of Aziridines

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Product Available at TCI from the Hammond-Xu Research Group

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