Abstract
A method has been developed for the in situ sulfidation of Pd/C under continuous flow. The approach provides a cheap, sustainable, and operationally convenient method for chemoselective conjugate reduction by continuous hydrogenation. High conversions and excellent selectivities were obtained for olefin reduction in α/β-unsaturated carbonyl compounds in the presence of hydrogenatively sensitive functionalities. The methodology was analyzed with a green metric system to highlight the sustainability features of the process.
Highlights
Over the past few decades there has been increasing pressure on pharmaceutical manufacturers to apply green metrics and improve efficiencies across the spectrum of chemical processes that they employ.1–3 an emphasis has been placed on the implementation of continuous manufacturing.4–9 As a result, many enabling technologies have become available to drive this new agenda.10–33 Catalytic heterogeneous hydrogenation is a key process technology that has benefitted from the growing popularity and commercial availability of miniaturised continuous hydrogenation reactors
Our strategy for developing a chemoselective conjugate reduction by continuous hydrogenation was inspired by a series of reports by Sajiki and co-‐workers, where various sulfur species were employed as additives in Pd/C catalysed hydrogenation in batch format
A procedure has been developed for the in situ sulfidation of Pd/C in continuous flow
Summary
Over the past few decades there has been increasing pressure on pharmaceutical manufacturers to apply green metrics and improve efficiencies across the spectrum of chemical processes that they employ.1–3 an emphasis has been placed on the implementation of continuous manufacturing.4–9 As a result, many enabling technologies have become available to drive this new agenda.10–33 Catalytic heterogeneous hydrogenation is a key process technology that has benefitted from the growing popularity and commercial availability of miniaturised continuous hydrogenation reactors. A number of approaches have been developed that utilise bisphosphine ligated CuH catalysts.51,52 These highly carbophilic reducing agents have seen great utility in the asymmetric conjugate reduction of a range of α/β-‐unsaturated carbonyl compounds including ketones,53 esters54 and carboxylic acids.55 To the best of our knowledge no continuous-‐flow procedure has been reported that capitalises on this approach.
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