507477-15-8Relevant academic research and scientific papers
Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones
Jiao, Zhiwei,Beiger, Jason J.,Jin, Yushu,Ge, Shaozhong,Zhou, Jianrong Steve,Hartwig, John F.
supporting information, p. 15980 - 15986 (2016/12/23)
The transition-metal-catalyzed α-arylation of carbonyl compounds is a widely practiced method for C-C bond formation. Several enantioselective versions of this process have been reported, but intermolecular, enantioselective coupling reactions of aryl electrophiles with α-fluoro carbonyl compounds have yet to be disclosed. We report enantioselective coupling of aryl and heteroaryl bromides and triflates with α-fluoroindanones catalyzed by palladium complexes of a BINOL-derived monophosphine and Segphos, respectively. The enolates were generated directly from α-fluoroindanones in the presence of potassium phosphate base during the reactions. We also report that reactions of α-fluorotetralones occur in high yields and enantioselectivities when conducted with enolates generated by elimination of trifluoroacetate from trifluoromethyl β-diketone hydrates. These reactions were catalyzed by palladium complexes of the commercially available bisphosphine Difluorphos. Thus, the formation of enantioenriched α-aryl-α-fluoroketones can be readily achieved by C-C bond formation when the appropriate palladium catalyst and α-fluoro enolate precursor were used.
Direct α-fluorination of ketones using N-F reagents
Stavber, Stojan,Jereb, Marjan,Zupan, Marko
, p. 2609 - 2615 (2007/10/03)
The use of 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Accufluor NFTh) as a fluorine atom transfer reagent and methanol as solvent enabled direct regiospecific fluorofunctionalization of the α-carbonyl position in ketones w
