Regio- and Stereoselective Allylic Trifluoromethylation and Fluorination using CuCF3 and CuF Reagents
2013 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 78, no 14, 7330-7336 p.Article in journal (Refereed) Published
Copper-mediated trifluoromethylation of allylic chlorides and trifluoroacetates was performed using a convenient Cu-CF3 reagent. The reaction is suitable for selective synthesis of allyl trifluoromethyl species. Mechanistic studies indicate that the reaction proceeds via a nucleophilic substitution mechanism involving allyl copper intermediates. The analogous Cu-F reagent was suitable for fluorination of allyl chlorides. Stereodefined cyclic substrates reacted regio- and stereoselectively.
Place, publisher, year, edition, pages
2013. Vol. 78, no 14, 7330-7336 p.
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-94192DOI: 10.1021/jo4010074ISI: 000322210700055OAI: oai:DiVA.org:su-94192DiVA: diva2:652475
FunderSwedish Research CouncilKnut and Alice Wallenberg Foundation