Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation
2016 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 36, 5980-5989 p.Article in journal (Refereed) Published
A radical C-11-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into C-11-labelled amides, including the 11-HSD1 inhibitor [carbonyl-C-11]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated C-11-aminocarbonylation, which is limited to the preparation of C-11-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon-[C-11]CO delivery unit represents a simple and convenient alternative to previous radical C-11-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.
Place, publisher, year, edition, pages
2016. no 36, 5980-5989 p.
Radical reactions, Carbon isotopes, Carbon monoxide, Xenon, Radical initiator, Reductive dehalogenation, Radiochemistry, Carbonylation
IdentifiersURN: urn:nbn:se:uu:diva-316439DOI: 10.1002/ejoc.201601106ISI: 000392534600010OAI: oai:DiVA.org:uu-316439DiVA: diva2:1077882
FunderCarl Tryggers foundation , CTS13:333/14:356