Abstract

Telescoping the Synthesis and Reactions of Alpha-Diazocarbonyl Compounds in Flow

Anita Maguire, Professor of Pharmaceutical Chemistry, University College Cork

While alpha-diazocarbonyl compounds are extremely versatile intermediates in organic synthesis, enabling a wide range of powerful synthetic transformations under relatively mild conditions,  their use at scale is limited by safety concerns, in particular in relation to potentially hazardous precursors such as sulfonyl azides or diazoalkanes. Generation of sulfonyl azides in flow and their use in diazo transfer to form a wide range of alpha-diazocarbonyl compounds has been demonstrated through a range of protocols depending on the substrate structure. Furthermore, the successful telescoping of these steps with subsequent transformations including enantioselective transition metal catalysed reactions has been demonstrated. Thus, the synthetic potential of alpha-diazocarbonyl compounds can be accessed without isolating or handling either the sulfonyl azide or the alpha-diazocarbonyl compound.