Mechanistic study of in situ generation and use of methanesulfonyl azide as a diazo transfer reagent with real-time monitoring by FlowNMR

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Mechanistic study of in situ generation and use of methanesulfonyl azide as a diazo transfer reagent with real-time monitoring by FlowNMR

Lynch, Denis; O'Mahony, Rosella M.; McCarthy, Daniel G.; Bateman, Lorraine M.; Collins, Stuart G.; Maguire, Anita R.
Date: 2019-05-07
Copyright: © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version an article which has been published in final form in the European Journal of Organic Chemistry: https://doi.org/10.1002/ejoc.201900184. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Related: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201900184
Full text restriction information: Access to this article is restricted until 12 months after publication by request of the publisher
Restriction lift date: 2020-05-07
Citation: Lynch, D., O'Mahony, R. M., McCarthy, D. G., Bateman, L. M., Collins, S. G. and Maguire, A. R. (2019) 'Mechanistic Study of In Situ Generation and Use of Methanesulfonyl Azide as a Diazo Transfer Reagent with Real-Time Monitoring by FlowNMR', European Journal of Organic Chemistry, 2019(22), pp. 3575-3580. doi: 10.1002/ejoc.201900184
Published Version: 10.1002/ejoc.201900184

Abstract:

The mechanistic pathway by which the hazardous diazo transfer reagent methanesulfonyl azide can be formed in situ, from methanesulfonyl chloride and aqueous sodium azide, has been investigated using real-time reaction monitoring by FlowNMR. In the presence of triethylamine, rapid generation of methanesufonyl azide is observed, via a mechanistic pathway consistent with involvement of a sulfene or methanesulfonyl triethylammonium intermediate. Accordingly, it is possible to generate and use methanesulfonyl azide in a single synthetic step for a diazo transfer process.

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