Synthesis of cyclic alpha-diazo-beta-keto sulfoxides in batch and continuous flow

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Synthesis of cyclic alpha-diazo-beta-keto sulfoxides in batch and continuous flow

McCaw, Patrick G.; Buckley, Naomi M.; Eccles, Kevin S.; Lawrence, Simon E.; Maguire, Anita R.; Collins, Stuart G.
Date: 2017-03-08
Copyright: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acs.joc.7b00172
Full text restriction information: Access to this article is restricted until 12 months after publication by the request of the author.
Restriction lift date: 2018-03-08
Citation: McCaw, P. G., Buckley, N. M., Eccles, K. S., Lawrence, S. E., Maguire, A. R. and Collins, S. G. (2017) 'Synthesis of cyclic alpha-diazo-beta-keto sulfoxides in batch and continuous flow', Journal of Organic Chemistry, 82(7), pp. 3666-3679. doi:10.1021/acs.joc.7b00172
Published Version: 10.1021/acs.joc.7b00172

Abstract:

Diazo transfer to beta–keto sulfoxides to form stable isolable alpha-diazo-beta-keto sulfoxides has been achieved for the first time. Both monocyclic and benzofused ketone derived beta-keto sulfoxides were successfully explored as substrates for diazo transfer. Use of continuous flow leads to isolation of the desired compounds in enhanced yields relative to standard batch conditions, with short reaction times, increased safety profile and potential to scale up.

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