Telescoped diazo transfer and rhodium-catalysed S-H insertion in continuous flow

Kearney, Aoife M.; Lynch, Dennis; Collins, Stuart G.; Maguire, Anita R.

Telescoped diazo transfer and rhodium-catalysed S-H insertion in continuous flow

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1-s2.0-S0040403921007140-mmc1.pdf(2.37 MB)

Supplementary data

Date

2021-09-29

Authors

Kearney, Aoife M.

Lynch, Dennis

Collins, Stuart G.

Maguire, Anita R.

Publisher

Elsevier

Published Version

10.1016/j.tetlet.2021.153438

Abstract

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.

Keywords

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

Citation

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