C-H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow.
Authors
Greb, Andreas
Crespin, Lorène NS
Poh, Jian-Siang
Pasau, Patrick
Blakemore, David C
Ley, Steven V
Publication Date
2018-10-16Journal Title
Chem Commun (Camb)
ISSN
1359-7345
Publisher
Royal Society of Chemistry (RSC)
Volume
54
Issue
83
Pages
11685-11688
Language
eng
Type
Article
Physical Medium
Print
Metadata
Show full item recordCitation
Dingwall, P., Greb, A., Crespin, L. N., 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
Abstract
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.
Keywords
aldehydes, unsymmetrical ketones, diazo compounds, flow chemistry, photochemistry
Sponsorship
ERC funding, sponsorship from UCB and Pfizer, Cambridge Home and EU Scholarship Scheme
Funder references
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)
Identifiers
External DOI: https://doi.org/10.1039/c8cc06202a
This record's URL: https://www.repository.cam.ac.uk/handle/1810/282978
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