138744-94-2Relevant academic research and scientific papers
Visible Light Mediated Reductive Cleavage of C-O Bonds Accessing α-Substituted Aryl Ketones
Speckmeier, Elisabeth,Padié, Clément,Zeitler, Kirsten
supporting information, p. 4818 - 4821 (2015/10/12)
C-O σ-bonds in multifaceted benzoin derivatives can be effectively cleaved as acetates using catalytic amounts of [Ru(bpy)3]Cl2 as photoredox catalyst in combination with Hantzsch ester and triethylamine as a sacrificial electron donor. This mild and operationally simple method is applicable to a great variety of substrates. Homo- and cross-benzoins, which are easily accessed by NHC (N-heterocyclic carbene) catalysis, with both electron-withdrawing and electron-donating substituents, including aryl halogenides, can be employed. The deoxygenated counterparts are isolated in good to excellent yields. These broadly accessible, α-substituted (nonsymmetric) aryl ketones are versatilely applicable for further transformations as illustrated by the syntheses of 2-arylbenzofurans.
Palladium-catalyzed oxidation of benzyl ketones to synthesis of α-acetoxy ketones using molecular oxygen
Chen, Zheng-Wang,Ye, Dong-Nai,Ye, Min,Liu, Liang-Xian
supporting information, p. 1388 - 1390 (2013/11/19)
An efficient procedure for the preparation of α-acetoxy ketone derivatives by palladium-catalyzed oxidation reactions employing molecular oxygen as the sole oxidant has been reported. A variety of benzyl ketones were used to investigate the scope of the r
Metal-free reductive cleavage of C-O σ-bonds in acyloin derivatives by an organic neutral super-electron-donor
Cutulic, Sylvain P. Y.,Findlay, Neil J.,Zhou, Sheng-Ze,Chrystal, Ewan J. T.,Murphy, John A.
supporting information; experimental part, p. 8713 - 8718 (2009/12/28)
(Chemical Equation Presented) Neutral organic electron-donor 7, formally a pyridinylidene carbene dimer, effects reductive cleavage of C-O σ-bonds in acyloin derivatives Ar(CO)CRR′OX (X = OAc, OPiv, OBz, OMs) and this represents the first cleavage of C-O σ-bonds by a neutral organic electron-donor. The methodology is applicable to a large array of substrates and the reduced counterparts were isolated in good to excellent yields. For certain substrates, donor 7 behaves as a base, effecting condensation reactions with some acetate ester derivatives of acyloins, leading to butenolides. The variation in reactivity among the different substrates was rationalized. 2009 American Chemical Society.
Chemoselective control of hydrogenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst
Hattori, Kazuyuki,Sajiki, Hironao,Hirota, Kosaku
, p. 4817 - 4824 (2007/10/03)
The hydrogenolysis of aromatic ketones and aldehydes quite smoothly give the corresponding methylene compounds via the formation of the intermediary benzyl alcohols in the presence of Pd/C as a catalyst. Therefore, it is extremely difficult to isolate the intermediary benzyl alcohol selectively. This paper describes a mild and chemoselective hydrogenation method of an aromatic carbonyl compound to benzyl alcohol using the 10% Pd/C(en) catalyst and its application to the chemoselective deacetoxylation reaction at the benzylic position in the presence of the benzyl alcohol functionality within the molecule.
PHASE-TRANSFER CATALYZED PERMANGANTE OXIDATIONS USING TRISAMINE (TDA-1)
McKillop, Alexander,Mills, Lester S.
, p. 647 - 656 (2007/10/02)
Oxidation of arylmethanols with KMnO4/TDA-1 under phase-transfer conditions at room temperature gives good to excellent yields of benzaldehydes.A number of other functional groups are also oxidised efficiently with the same reagent system.
Reaction of α,β-Unsaturated Carboxylic Acids with Manganese(III) Acetate in the Presence of Chloride Ion
Yonemura, Hiroshi,Nishino, Hiroshi,Kurosawa, Kazu
, p. 3153 - 3160 (2007/10/02)
The reaction of 3-phenylpropenoic acids with manganese(III) acetate - Cl- complex yielded 1,2,2-trichloro-1-phenylethanes, 1-acetoxy-2,2-dichloro-1-phenylethanes, and 2,2-dichloro-1-phenylethanols. (E)-2,3-Diphenylpropenoic acids gave 2,2-dichloro-1,2-diphenylethanones and 2-acetoxy-1,2-diphenylethanones. 3,3-Diphenylpropenoic acids yielded 2,2-dichloro-1,1-diphenylethenes, 1-acetoxy-2,2-dichloro-1,1-diphenylethanes, 2,2-dichloro-1,1-diphenyl-1-ethanols, and 2-hydroxy-2,2-diphenylethanal.Fluorenylideneacetic acid gave 9-chloro-9-(dichloromethyl)fluorene, 9-acetoxy-9-(dichloromethyl)fluorene, and 9-fluorenone. 1-Cyclohexenecarboxylic acid yielded 1,2-dichlorocyclohexanecarboxylic acid and 1-acetoxy-2-chlorocyclohexanecarboxylic acid.The reaction can be explained in terms of a free-radical mechanism involving manganese(III) acetate - Cl- complexation, addition of Cl. radical, decarboxylation, and the oxidation of chloroethenes which are the reaction intermediates.
The α-Chlorination of Aryl Ketones with Manganese(III) Acetate in the presence of Chloride Ion
Tsuruta, Takehiko,Harada, Tetsuya,Nishino, Hiroshi,Kurosawa, Kazu
, p. 142 - 145 (2007/10/02)
The reaction of 2-(4-methoxyphenyl)-4-chromanone with Mn(OAc)3 in the presence of LiCl gave 3,3-dichloro-2-(4-methoxyphenyl)-4-chromanone.The reactions of 2-phenyl-4-chromanone, 1-phenyl-1-propanone, 1,2-diphenylethanone, and 1-tetralone similarly yielded α,α-dichloro derivatives in good yields. 2,2,2-Trichloroacetophenones were obtained from 2,2-dichloroacetophenones, but in the absence of LiCl, 2,2-dichloroacetophenones gave 2,2,3,3-tetrachloro-1,4-butanediones.KCl, NaCl, NH4Cl,AlCl3, and CaCl2 were also employed as the Cl- ion source.Synthetic applicability and the reaction mechanisms are discussed briefly.
