C-H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow.
Published version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Dingwall, Paul https://orcid.org/0000-0002-6961-7995
Greb, Andreas
Crespin, Lorène NS
Labes, Ricardo https://orcid.org/0000-0003-4001-0775
Musio, Biagia https://orcid.org/0000-0001-7799-5155
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.
Description
Keywords
aldehydes, unsymmetrical ketones, diazo compounds, flow chemistry, photochemistry
Journal Title
Chem Commun (Camb)
Conference Name
Journal ISSN
1359-7345
1364-548X
1364-548X
Volume Title
54
Publisher
Royal Society of Chemistry (RSC)
Publisher DOI
Sponsorship
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)
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)
ERC funding, sponsorship from UCB and Pfizer, Cambridge Home and EU Scholarship Scheme