C-H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow.
Blakemore, David C
Chem Commun (Camb)
Royal Society of Chemistry (RSC)
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Dingwall, P., Greb, A., Crespin, L., Labes, R., Musio, B., Poh, J., Pasau, P., et al. (2018). C-H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow.. Chem Commun (Camb), 54 (83), 11685-11688. https://doi.org/10.1039/c8cc06202a
The difficulty in accessing and safely utilising non-stabilised diazo species has in the past limited the application of this class of compounds. Here we explore further the use of oxadiazolines, non-stabilised diazo precursors which are bench stable, in direct, non-catalytic, aldehyde C-H functionalisation reactions under UV photolysis in flow and free from additives. Commercially available aldehydes are coupled to afford unsymmetrical aryl-alkyl and alkyl-alkyl ketones while mild conditions and lack of transition metal catalysts allow for exceptional functional group tolerance. Examples are given on small scale and in a larger scale continuous production.
ERC funding, sponsorship from UCB and Pfizer, Cambridge Home and EU Scholarship Scheme
Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/M004120/1)
European Commission Horizon 2020 (H2020) Future and Emerging Technologies (FET) (737266)
Engineering and Physical Sciences Research Council (EP/K039520/1)
External DOI: https://doi.org/10.1039/c8cc06202a
This record's URL: https://www.repository.cam.ac.uk/handle/1810/282978
Attribution 4.0 International
Licence URL: https://creativecommons.org/licenses/by/4.0/