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Syn-3-Fluoro-4-aminopiperidine- a story from multiple orientations

If Nature could re-write her proteinogenic amino acid instruction manual I’m fairly sure that a piperidine ring would feature in there somewhere. Perhaps in the spirit of less is more the pyrrolidine ring won out. Not so for human synthetic engineers- the piperidine ring is ubiquitous in pharmaceuticals, agrochemicals and advanced materials and is the

Light-driven Deoxyfluorination of Alcohols with Seletfluor

Deoxyfluorination remains amongst the most frequently used method for preparing alkyl fluoro compounds.1 The reaction typically involves activation of a leaving group followed by SN2 (but occasionally SN1) reaction with fluoride ion. This is usually accompanied with significant elimination side-reactions and can frequently be low yielding. The original deoxyfluorination reagents such as DAST (diethylaminosulfur-trifluoride) and

Fluorine and sulfur- an old combination with a new lease of life

The use of fluorine and fluorine-containing functional groups in medicinal chemistry, agrochemicals and advanced materials has grown over the past fifty years.1 Not surprisingly this increase in utility tracks with notable developments and refinements in safe and accessible synthetic methodology, both on the discovery and development front and in subsequent manufacturing. A recent example that caught

The Balz-Schiemann Reaction

Aryl- and heteroaryl- diazonium tetrafluoroborate salts, prepared by diazotization of an aniline in the presence of HBF4, are unique in that in many cases they are sufficiently stable to isolate. Thermal decomposition of these salts at elevated temperatures results in fluoro-dediazoniation and formation of the corresponding aryl or heteroaryl fluoride- the Balz-Schiemann reaction.1a,bRadiolabelled 18F compounds

Fluoride Sources for Halex Reactions

The halex reaction is a great way to introduce a fluorine atom in to an aromatic ring, but the reaction often requires high temperatures and or long reaction times if metal fluorides are used.  Tetralkylammonium fluorides are a better option due to their higher solubility in the reaction medium, however these salts are often hydrated

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