1628218-89-2Relevant academic research and scientific papers
Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes
Wu, Guojiao,Jacobi Von Wangelin, Axel
, p. 1795 - 1802 (2018)
Stereoselective additions of highly functionalized reagents to available unsaturated hydrocarbons are an attractive synthetic tool due to their high atom economy, modularity, and rapid generation of complexity. We report efficient cobalt-catalyzed (E)-halofluoroalkylations of alkynes/alkenes that enable the construction of densely functionalized, stereodefined fluorinated hydrocarbons. The mild conditions (2 mol% cat., 20 °C, acetone/water, 3 h) tolerate various functional groups, i.e. halides, alcohols, aldehydes, nitriles, esters, and heteroarenes. This reaction is the first example of a highly stereoselective cobalt-catalyzed halo-fluoroalkylation. Unlike related cobalt-catalyzed reductive couplings and Heck-type reactions, it operates via a radical chain mechanism involving terminal halogen atom transfer which obviates the need for a stoichiometric sacrificial reductant.
Copper-mediated direct functionalization of unsaturated C-C bonds with ethyl bromo(difluoro)acetate: A straightforward access to highly valuable difluoromethylated alkenes
Belhomme, Marie-Charlotte,Dru, Delphine,Xiong, Heng-Ying,Cahard, Dominique,Besset, Tatiana,Poisson, Thomas,Pannecoucke, Xavier
supporting information, p. 1859 - 1870 (2014/07/22)
A copper-mediated fluorofunctionalization of alkenes and alkynes has been developed. This method provides ready access to trisubstituted difluoromethylated olefins (from dihydropyrans, glycal derivatives, or terminal alkynes) or to tetrasubstituted olefins (from disubstituted alkynes). The products were obtained in good to high yields with acceptable E/Z selectivities. Finally, a first direct route to difluoromethylated alkynes is reported, albeit with low yields. Georg Thieme Verlag Stuttgart New York.
