Telescoped diazo transfer and rhodium-catalysed S-H insertion in continuous flow
Kearney, Aoife M.
Collins, Stuart G.
Maguire, Anita R.
Rhodium-catalysed S–H insertion of α-diazo-γ-butyrolactams has been successfully telescoped using continuous processing with in situ generated triflyl azide in flow and deacylative diazo transfer, incorporating real-time reaction monitoring of the final process outflow by IR spectroscopy. Significantly, the α-diazo-γ-butyrolactam reaction stream was sufficiently pure to progress to the rhodium-catalysed S–H insertion step without detrimental impact on the rhodium catalyst or the reaction efficiency.
Diazo transfer , Telescoped continuous processes , Rhodium carboxylate catalyst , Taming hazardous chemistry , Trifluoromethanesulfonyl azide , Alpha-sulfonyl , Triflyl azide , Safe , Generation , Efficient , Reagent , α-Diazolactams , S–H insertion
Kearney, A., Lynch, D., Collins, S. and Maguire, A. (2021) ‘Telescoped diazo transfer and rhodium-catalysed S–H insertion in continuous flow’, Tetrahedron Letters, 83, 153438 (4 pp). doi: 10.1016/j.tetlet.2021.153438