6453-95-8Relevant academic research and scientific papers
Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes
Fujita, Takeshi,Kinoshita, Ryo,Takanohashi, Tsuyoshi,Suzuki, Naoto,Ichikawa, Junji
, p. 2682 - 2689 (2017)
1,1-Difluoro-1-alkenes bearing a biaryl-2-yl group effectively underwent site-selective intramolecular iodoarylation by the appropriate cationic iodine species. Iodoarylation of 2-(2-aryl-3,3-difluoroallyl)biaryls proceeded via regioselective carbon-carbon bond formation at the carbon atoms in β-position to the fluorine substituents, thereby constructing dibenzo-fused six-membered carbocycles bearing a difluoroiodomethyl group. In contrast, 2-(3,3-difluoroallyl)biaryls underwent a similar cyclization at the α-carbon atoms to afford ring-difluorinated seven-membered carbocycles.
Charge delocalization from cationic substituents into phenanthrene: Variation in response among regioisomeric carbocations and carboxonium ions
Laali, Kenneth K.,Hollenstein, Sandro
, p. 897 - 904 (1998)
In an effort to assess charge delocalization and stabilities, a series of regioisomeric PAH-C+R2 carbocations (PAH = phenanthrene; R = Me, Ph) were generated from their alcohols by ionization with FSO3H/SO2ClF.
Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination
Martins, Bruna S.,Kaiser, Daniel,Bauer, Adriano,Tiefenbrunner, Irmgard,Maulide, Nuno
, p. 2094 - 2098 (2021/04/05)
A formal enone α-arylation is described. This metal-free transformation relies on the I(III)-mediated skeletal reorganization of silyl enol ethers and features mild conditions, good yields, and high stereoselectivities for β-substituted enones.
Arylation of Aldehydes to Directly Form Ketones via Tandem Nickel Catalysis
Lei, Chuanhu,Zhu, Daoyong,Tangcueco, Vicente Iii Tiu,Zhou, Jianrong Steve
supporting information, p. 5817 - 5822 (2019/08/26)
A nickel-catalyzed arylation of both aliphatic and aromatic aldehydes proceeds with air-stable (hetero)arylboronic acids, with an exceptionally wide substrate scope. The neutral condition tolerates acidic hydrogen and sensitive polar groups and also preserves α-stereocenters of some chiral aldehydes. Interestingly, this nickel(0) catalysis does not follow common 1,2-insertion of arylmetal species to aldehydes and β-hydrogen elimination.
Synthesis of Phenanthrenes through Visible-Light Photoredox Catalyzed Intramolecular Cyclization of α-Bromochalcones
Nagode, Savita B.,Kant, Ruchir,Rastogi, Namrata
supporting information, p. 1533 - 1537 (2018/04/20)
A mild and efficient photocatalytic protocol for the synthesis of the phenanthrene scaffold has been devised. The reaction involves intramolecular cyclization of α-keto vinyl radicals generated from α-bromochalcones under visible light photoredox catalyze
Iron-catalyzed tandem carbon-carbon/carbon-oxygen bond formation/aromatization of 2′-alkynyl-biphenyl-2-carbinols: A new approach to the synthesis of substituted phenanthrenes
Bera, Krishnendu,Sarkar, Soumen,Jana, Umasish
supporting information, p. 312 - 315 (2015/03/05)
An iron-catalyzed efficient synthesis of substituted phenanthrenes through tandem intramolecular C-C/C-O bond formations/aromatization of 2′-alkynyl-biphenyl-2-carbinols is reported. This method provides a novel, highly efficient, and straightforward rout
Synthesis of substituted phenanthrene by iron(III)-catalyzed intramolecular alkyne-carbonyl metathesis
Bera, Krishnendu,Sarkar, Soumen,Jalal, Swapnadeep,Jana, Umasish
, p. 8780 - 8786 (2012/11/07)
An efficient synthesis of functionalized phenanthrenes has been developed for the first time involving an iron(III)-catalyzed intramolecular coupling of 2′-alkynyl-biphenyl-2-carbaldehydes. A broad range of functionalized phenanthrene derivatives could be
Synthesis of ketones from α-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling
Goossen, Lukas J.,Rudolphi, Felix,Oppel, Christoph,Rodriguez, Nuria
, p. 3043 - 3045 (2008/12/23)
(Chemical Equation Presented) The power of two metals: A Pd/Cu catalyst system mediates the in situ formation of acyl nucleophiles by decarboxylation of readily accessible and stable salts of α-oxocarboxylic acids and their cross-coupling with aryl or heteroaryl bromides to give ketones. The reaction may be usedin the presence of many functional groups and provides good yields.
The Mg-oppenauer oxidation as a mild method for the synthesis of aryl and metallocenyl ketones
Kloetzing, Ralf J.,Krasovskiy, Arkady,Knochel, Paul
, p. 215 - 227 (2007/10/03)
Magnesium alkoxides undergo a hydride-transfer oxidation with benzaldehyde as the oxidant. This magnesium variant of the Oppenauer oxidation was used for the synthesis of polyfunctional biaryl ketones. LiCl was found to promote this reaction by enhancing the solubility of magnesium alkoxides. This mild oxidation method was especially useful for preparing ketones bearing a metallocenyl unit as well as various new ferrocenyl ketones and tricarbonylchromium complexes. This last class of ketones was reduced with the CBS catalyst (CBS = Corey-Bakshi-Shibata, diphenyl oxazaborolidine) to chiral benzhydrol complexes with high enantioselectivity enabling an asymmetric synthesis of electronrich or -poor benzhydryl alcohols (up to 94% ee).
Nickel-catalyzed coupling of aryl iodides with aromatic aldehydes: Chemoselective synthesis of ketones
Huang, Yi-Chun,Majumdar, Kanak Kanti,Cheng, Chien-Hong
, p. 1682 - 1684 (2007/10/03)
Aryl iodide (ArI) couple with aryl aldehydes (Ar'CHO) in the presence of Ni(dppe)Br2 and Zn to give the corresponding biaryl ketones (ArCOAr′). The use of a bidentate phosphine complex is critical to the success of this catalytic reaction. The
