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Singing in the Rain- Removing Residual Lithium Salts From Flow Reactors Under Anhydrous Conditions

Organolithium reagents are powerful and ubiquitous intermediates used extensively in synthetic chemistry both in academic and industrial settings. The stability of these reagents often necessitates generation and rapid processing at cryogenic temperatures: some organolithium species are chemically or configurationally unstable at temperatures above -100°C. An example is the dichloromethyllithium anion generated during the Mattison homologation

Per-and Polyfluorinated Alkyl (PFAS) Substances: Ubique Perpetuum

In December 2023 Nick Tyrell from ALMAC gave an interesting and timely presentation at our Winer Process Chemistry Conference in Liverpool, UK on the proposed EU ban of all per– and poly-fluorinated materials, including polymers and the fluorinating reagents we use routinely to introduce fluorine or fluorine-containing functional groups into complex molecules. The details of

Less is More- Deletion, Insertion and Everything In-Between

Single atom deletion and skeletal editing of complex organic molecules is an interesting and potentially very impactful area of research. Over 100 papers mentioning the term ‘skeletal editing’ have been published in the past 2 years. The ability to selectively add or remove a single heteroatom from a molecules core architecture is distinctly different from

These Are Tri(azol)ing Times…. Great Chemistry- But Do Not Attempt on a Damp Day

Five-membered heterocyclic arenes account for a large portion of the heterocycles found in pharmaceuticals and bioactive molecules.1 Synthesis of heteroaryl halides and elaboration via metal catalysed cross coupling reactions- particularly with aliphatic amines- is, however, known to be challenging. These small heterocycles-particularly electron-rich systems- frequently coordinate to palladium, promoting catalyst deactivation via displacement of the supporting

One Functional Group, So Many Functions

The complex machinery required to take a drug through development and regulatory approval can be as arduous as the discovery of the molecule itself. In recent times the demand for COVID-19 drugs has added to the pressure to expedite this process in record time and several organizations working in the small molecule arena have met

Not a Dry Eye in the House

Yesterday I glanced through the list of drugs approved by the FDA in Q2 2023. One in particular, Miebo,1 -developed by Bausch and Lomb- made me sit up and stare. The compound is a partially fluorinated alkane (1-(Perfluorohexyl)octane, Figure 1) and is administered directly into the eye as a neat, anhydrous liquid to treat dry

Hey Phenol- Everyone has their Cross to Bear

Tert-butyl phenols are important commodity chemicals, with annual production exceeding 120,000 t per annum. They have multiple industrial applications including agrochemicals, antioxidants- in particular 2,6-di-tert-butyl-4- methylphenol (BHT, Figure 1), foods, flavours and fragrances and pharmaceuticals.1 BHT in particular, used as an antioxidant in polymers and oils and prepared by reaction of p-cresol with isobutylene in

The Germanes Have It

A couple of weeks ago I attended the 20th annual Bristol Synthesis Meeting at the Victoria rooms in Bristol, UK.1 Always an excellent event, and this one was no exception. I was intrigued by a presentation given by Franziska Schoenebeck from the University of Aachen, Germany on the application of organogermanes in cross coupling chemistry.

Ant Music

I don’t usually post articles on total synthesis. Their beauty often speaks for itself. However, a recent paper by Zhang and co-workers started me on a trip down memory lane. The paper describes a short, elegant route into the core 1-azabicyclo[4.3.0]nonane structure of the Indolizidine alkaloids (figure 1).1 Together with the structurally related pyrrolizidines (1-azabicyclo[3.3.0]octane),

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