Abstract

Enhancing the Synthetic Utility of alpha-Diazocarbonyl Compounds Through Use of Continuous Flow Technology

Anita Maguire, Professor of Pharmaceutical Chemistry, University College Cork

While alpha-diazocarbonyl compounds are extremely versatile intermediates in organic synthesis, their use at scale is limited by safety concerns, in particular in relation to potentially hazardous precursors such as sulfonyl azides or diazoalkanes. Recent results from the team will be presented showing that sulfonyl azides can be generated in flow and used directly in diazo transfer to form a wide range of alpha-diazocarbonyl compounds. Furthermore, the successful telescoping of these steps with subsequent enantioselective transition metal catalyzed 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. Five distinct protocols for diazo transfer in continuous flow have been developed, ensuring broad applicability across a range of substrates.