1355165-68-2Relevant 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.
, 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.
Palladium-catalyzed direct α-arylation of α-fluoroketones: A straightforward route to α-fluoro-α-arylketones
Guo, Chen,Wang, Ruo-Wen,Guo, Yong,Qing, Feng-Ling
experimental part, p. 86 - 96 (2012/02/05)
The palladium-catalyzed direct α-arylation of both open-chain and cyclic α-fluoroketones by using P(o-tolyl)3 or RuPhos as ligand and K3PO4·3H2O as mild base has been developed. This method allows a variety of q
