Some of the most used carbon feedstock materials in chemical industry are gaseous at room temperature. Although macroscale processes employ very well-established techniques to handle reactive and even dangerous gases, a very different picture is seen in lab-scale research. The purchase and storage of lecture bottles poses an inherent risk due to the high pressures, not to mention the costs of transport and disposal. Pioneered by the Skrydstrup group in 2011, two-chamber reactors have been proposed as an alternative technology to engage synthetic gases in a safe and near-stoichiometric amount. With carbon monoxide as the flagship gas, several CO-insertion reactions were discovered using safe and bench-stable CO precursors. Our own lab has recently proposed the most cost-effective CO generating system to date, with formic acid as the source of the gas molecule. Using this technique, an intramolecular carbonylative C-H activation of 1,2,3-triazoles was discovered, enabling the preparation of a variety of novel heterocyclic scaffolds. Moving away from carbon monoxide, precursors to other synthetic gases were sought after. A straightforward generation of sulfur dioxide (SO2) was developed, which was subsequently used to produce large amounts of the DABSO reagent. Lastly, sulfuryl fluoride (SO2F2) was employed in a two-chamber set-up to transform phenols into aryl fluorosulfates: useful reagents as triflate surrogates or as SuFEx click partners.

Convenient handling of reactive gases: Methods for carbonylation and fluorosulfate synthesis

256th National Meeting (2018)

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