102781-44-2Relevant articles and documents
Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids
Bandar, Jeffrey S.,Ascic, Erhad,Buchwald, Stephen L.
supporting information, p. 5821 - 5824 (2016/06/09)
A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diastereoselective ketone reduction cycle. Symmetrical aryl carboxyclic anhydrides provide access to enantioenriched α-substituted ketones or alcohols with excellent stereoselectivity and functional group tolerance.
Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium
Dobmeier, Michael,Herrmann, Josef M.,Lenoir, Dieter,Koenig, Burkhard
supporting information; experimental part, p. 330 - 336 (2012/05/20)
The synthetic protocol for the reduction of alcohols to hydrocarbons by using hydriodic acid, first described by Kiliani more than 140 years ago, was improved to be more applicable to organic synthesis. Instead of a strongly acidic, aqueous solution, a biphasic toluene-water reaction medium was used, which allowed the conversion of primary, secondary and tertiary benzylic alcohols, in good yields and short reaction times, into the corresponding hydrocarbons. Red phosphorous was used as the stoichiometric reducing agent. Keto, ester, amide or ether groups are tolerated, and catalytic amounts of hydriodic acid (0.2 equiv) in the presence of 0.6 equiv phosphorous are sufficient to achieve conversion.
A mild oxidative aryl radical addition into alkenes by aerobic oxidation of arylhydrazines
Taniguchi, Tsuyoshi,Zaimoku, Hisaaki,Ishibashi, Hiroyuki
experimental part, p. 4307 - 4312 (2011/05/07)
A mild and practical oxyarylation of alkenes by oxidative radical addition has been developed by using aerobic oxidation of hydrazine compounds. The use of a catalytic amount of potassium ferrocyanide trihydrate (K4[Fe(CN) 6]·3 H2O) and water accelerated this radical reaction to give peroxides or alcohols from simple alkenes in good yields. The environmentally friendly and economical radical reactions were achieved at room temperature in the presence of iron catalyst, oxygen gas, and water. A method involving aniline as a radical precursor is also described. Copyright
MECANISME DE L'ADDITION NUCLEOPHILE AU GROUPEMENT CARBONYLE-I. INFLUENCE DE LA NATURE DU SUBSTITUANT POLAIRE SUR LA STEREOCHIMIE ET LA REACTIVITE DANS LES REACTIONS D'ADDITION DE BROMURE DE METHYLMAGNESIUM AUX ARYL-1 PHENYL-2 PROPANONES
Lasperas, M.,Perez-Rubalcaba, A.,Quiroga-Feijoo, M. L.
, p. 3403 - 3408 (2007/10/02)
The influence of a m- or p-polar substituent in 1-aryl 2-phenyl propanones, on addition reactions with CH3MgBr in ether at 30 deg C has been investigated.The invariability of asymmetric induction as a function of substituent, and the correlation of rate constant ratios with Hammett ? constants (ρ=0.24, r=0.97), are consistent with a four-centre pericyclic concerted mechanism with concomitant departure of a solvent molecule.
