Synthesis of cyclic alpha-diazo-beta-keto sulfoxides in batch and continuous flow
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Date
2017-03-08
Authors
McCaw, Patrick G.
Buckley, Naomi M.
Eccles, Kevin S.
Lawrence, Simon E.
Maguire, Anita R.
Collins, Stuart G.
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
Published Version
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.
Description
Keywords
Diazo transfer , Continuous flow , Amberlyst A21 , α-diazo-β-keto-sulfoxide
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
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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