Visible-Light-Enabled Aminocarbonylation of Unactivated Alkyl Iodides with Stoichiometric Carbon Monoxide for Application on Late-Stage Carbon Isotope Labeling

Malvika Sardana (1) , Joakim Bergman (1) , Cecilia Ericsson (1) , Lee Kingston (1) , Magnus Schou (2, 3) , Christophe Dugave (4) , Davide Audisio (4) , Charles Elmore (1)

1 AstraZeneca
2 Karolinska Institutet [Stockholm]
3 Stockholm County Council
4 SCBM - Service de Chimie Bio-Organique et de Marquage

A visible-light-mediated late-stage aminocarbonylation of unactivated alkyl iodides with stoichiometric amounts of carbon monoxide is presented. The method provides a mild, one-step route to [carbonyl-C-13/14] alkyl amides, thereby reducing radioactive waste, and handling of radioactive materials. Easily accessible and low-cost equipment and a palladium catalyst were successfully used for the synthesis of a wide range of alkyl amides.

Keywords: Spectrometry

Domains: Chemical Sciences; Radiochemistry; Organic chemistry

Malvika Sardana, Joakim Bergman, Cecilia Ericsson, Lee Kingston, Magnus Schou, et al.. Visible-Light-Enabled Aminocarbonylation of Unactivated Alkyl Iodides with Stoichiometric Carbon Monoxide for Application on Late-Stage Carbon Isotope Labeling. Journal of Organic Chemistry, 2019, 84 (24), pp.16076-16085. ⟨10.1021/acs.joc.9b02575⟩. ⟨cea-02488945⟩