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

2021

October

Tetrahedron Letters

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

Published

WOS: 2 ()

Diazo transfer α-Diazolactams S–H insertion Telescoped continuous processes Rhodium carboxylate catalyst Taming hazardous chemistry Trifluoromethanesulfonyl azide Alpha-sulfonyl Triflyl azide Safe Generation Efficient Reagent

83

153438

Rhodium-catalysed S-H insertion of alpha-diazo-gamma-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 alpha-diazo-gamma-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. (C) 2021 The Author(s). Published by Elsevier Ltd.

OXFORD

0040-4039

10.1016/j.tetlet.2021.153438