745033-23-2Relevant academic research and scientific papers
Palladacycle-Phosphine Catalyzed Methylation of Amines and Ketones Using Methanol
Mamidala, Ramesh,Biswal, Priyabrata,Subramani, M. Siva,Samser, Shaikh,Venkatasubbaiah, Krishnan
, p. 10472 - 10480 (2019/08/20)
Methylation of amines and ketones with palladacycle precatalyst has been performed using methanol as an environmentally benign reagent. Various ketones and amines undergo methylation reaction to yield monomethylated amines or ketones in moderate to good isolated yields. Moreover, this protocol was tested for the chemoselective methylation of 4-aminobenzenesulfonamide. The scope of the reaction was further extended to the deuteromethylation of ketones.
α-Methylation of Ketones with Methanol Catalyzed by Ni/SiO2-Al2O3
Charvieux, Aubin,Duguet, Nicolas,Métay, Estelle
supporting information, p. 3694 - 3698 (2019/06/13)
α-Methylation of ketones with methanol catalyzed by a cheap and easy to handle Ni/SiO2-Al2O3 was explored. After optimization of the reaction between propiophenone and methanol, the desired product was obtained in 95 % isolated yield. A wide range of ketones was methylated under the optimized conditions (16 examples). This procedure was extended to a three-component cross-benzylation-methylation of acetophenone.
B(C6F5)3-Catalyzed Highly Stereoselective Hydrogenation of Unfunctionalized Tetrasubstituted Olefins
Dai, Yun,Feng, Xiangqing,Du, Haifeng
supporting information, p. 6884 - 6887 (2019/10/02)
A metal-free hydrogenation of unfunctionalized tetrasubstituted olefins were successfully realized using a combination of B(C6F5)3 and Ph2NMe catalyst. The corresponding products were afforded in 58-98% yields with up to >99:1 cis/trans selectivity.
Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers
Paladhi, Sushovan,Liu, Yidong,Kumar, B. Senthil,Jung, Min-Jung,Park, Sang Yeon,Yan, Hailong,Song, Choong Eui
supporting information, p. 3279 - 3282 (2017/06/23)
The potential of Song's chiral oligoethylene glycols (oligoEGs) as catalysts was explored in the enantioselective protonation of trimethylsilyl enol ethers in combination with alkali metal fluoride (KF and CsF) and in the presence of a proton source. Highly enantioselective protonations of various silyl enol ethers of α-substituted tetralones were achieved, producing chiral α-substituted tetralones in full conversion and with up to 99% ee. The established protocol was successfully extended to the synthesis of biologically relevant chiral α-substituted chromanone and thiochromanone derivatives.
DMF Dimethyl Acetal as Carbon Source for α-Methylation of Ketones: A Hydrogenation-Hydrogenolysis Strategy of Enaminones
Borah, Ashwini,Goswami, Limi,Neog, Kashmiri,Gogoi, Pranjal
, p. 4722 - 4728 (2015/05/13)
A novel heterogeneous catalytic hydrogenation-hydrogenolysis strategy has been developed for the α-methylation of ketones via enaminones using DMF dimethyl acetal as carbon source. This strategy provides a very convenient route to α-methylated ketones using a variety of ketones without any base or oxidant. (Chemical Equation Presented).
Enantioselective protonation of alkenyl trifluoroacetates catalyzed by chiral tin methoxide
Yanagisawa, Akira,Sugita, Takuya,Yoshida, Kazuhiro
, p. 16200 - 16203 (2013/12/04)
Go catalytic! A catalytic enantioselective protonation of alkenyl trifluoroacetates was achieved by using an in situ generated chiral tin bromide methoxide as the chiral catalyst in the presence of methanol (see scheme). Optically active ketones containing a tertiary stereogenic center at the α-position were obtained with enantioselectivities of up to 94 % ee. Copyright
Urea activation of nitrimines: A mild, metal-free approach to sterically hindered enamines
Nickerson, David M.,Angeles, Veronica V.,Mattson, Anita E.
supporting information, p. 5000 - 5003 (2013/10/22)
Nitrimines have been identified as impressive starting points for the syntheses of otherwise inaccessible, sterically encumbered enamines. The activation of nitrimines with urea catalysts for reaction with a variety of amines enables the formation of high
Development of a chiral bis(guanidino)iminophosphorane as an uncharged organosuperbase for the enantioselective amination of ketones
Takeda, Tadahiro,Terada, Masahiro
supporting information, p. 15306 - 15309 (2013/11/06)
Chiral bis(guanidino)iminophosphoranes were designed and synthesized as chiral uncharged organosuperbase catalysts that facilitate activation of less-acidic pro-nucleophiles. The newly developed bis(guanidino) iminophosphoranes, which possess the highest basicity among chiral organocatalysts reported to date, were proven to be a superb class of chiral organosuperbases by reaction of azodicarboxylates with 2-alkyltetralones and their analogues as the less acidic pro-nucleophiles.
Synthesis of five- and six-membered benzocyclic ketones through intramolecular alkene hydroacylation catalyzed by Nickel(0)/N-Heterocyclic Carbenes
Hoshimoto, Yoichi,Hayashi, Yukari,Suzuki, Haruka,Ohashi, Masato,Ogoshi, Sensuke
, p. 10812 - 10815 (2013/01/15)
Getting some closure: Mechanistic studies supported the participation of an oxanickelacycle complex in the hydroacylation step of the title reaction, which proceeds without decarbonylation even in the absence of well-known chelation assistance by heteroatoms. Copyright
Catalytic enantioselective protonation of enol trifluoroacetates by means of hydrogenocarbonates and cinchona alkaloids
Claraz, Aurelie,Leroy, Jerome,Oudeyer, Sylvain,Levacher, Vincent
, p. 6457 - 6463 (2011/09/15)
Herein is disclosed an efficient catalytic enantioselective protonation of enol acetates by means of a readily implementable transition-metal-free chemical process. By making use of simple hygrogenocarbonates as the proton source and hydroquinine anthraquinone-1,4-diyl diether as the chiral proton shuttle, a series of cyclic enol trifluoroacetates are protonated under mild conditions to yield the corresponding ketones in up to 93% ee.
