86796-49-8Relevant academic research and scientific papers
CATALYTIC HYDROGENOLYSIS OF 1,1-DIFLUORO-2-PHENYL-AND 1,1-DIFLUORO-3-METHYL-2-PHENYLCYCLOPROPANE.
Isogai,Nishizawa,Saito,Sakai
, p. 1555 - 1556 (1983)
The title compounds were hydrogenolyzed over PdO or Raney nickel. The C//2-C//3 bond of the cyclopropane ring underwent cleavage exclusively over both catalyts. The contribution of the fluorine substituent to the lengthening and weakening the C//2-C//3 bond of the cyclopropane ring seems to become a dominant factor in regioselectivity.
Silver-catalyzed decarboxylative fluorination of aliphatic carboxylic acids in aqueous solution
Yin, Feng,Wang, Zhentao,Li, Zhaodong,Li, Chaozhong
supporting information; experimental part, p. 10401 - 10404 (2012/08/08)
Although fluorinated compounds have found widespread applications in the chemical and materials industries, general and site-specific C(sp3)-F bond formations are still a challenging task. We report here that with the catalysis of AgNO3, various aliphatic carboxylic acids undergo efficient decarboxylative fluorination with SELECTFLUOR reagent in aqueous solution, leading to the synthesis of the corresponding alkyl fluorides in satisfactory yields under mild conditions. This radical fluorination method is not only efficient and general but also chemoselective and functional-group- compatible, thus making it highly practical in the synthesis of fluorinated molecules. A mechanism involvinig Ag(III)-mediated single electron transfer followed by fluorine atom transfer is proposed for this catalytic fluorodecarboxylation.
