54881-85-5Relevant academic research and scientific papers
Nickel-catalyzed cross-coupling of styrenyl epoxides with boronic acids
Nielsen, Daniel K.,Doyle, Abigail G.
, p. 6056 - 6059 (2011/09/13)
Let's get multicatalytic! A Ni0 catalyst complexed with a biaryldialkyl monophosphine ligand facilitates C-C bond formation between styrenyl epoxides and aryl boronic acids (see scheme). X-ray analysis of a catalytically active nickel/ligand complex supports a redox pathway involving C sp 3-O bond activation. A variety of α-substituted alcohols were generated with good reaction efficiency by a multicatalytic sequence. Copyright
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.
Photochemically induced coupling reaction of triarylstibines with olefins
Kakusawa, Naoki,Tsuchiya, Takashi,Kurita, Jyoji
, p. 9743 - 9746 (2007/10/03)
Photoreaction of triarylstibines with styrenes resulted in the formation of 2-aryl-1-phenylethanols accompanied by air oxidation. Formation of the products has been explained by the valence expansion of the oxygen-antimony- styrene complex to a five-valent intermediate, followed by reductive coupling.
Mechanistic criteria for cation radical reactions: Aminium salt-catalyzed cyclopropanation
Yueh, Wang,Bauld, Nathan L.
, p. 5671 - 5676 (2007/10/02)
Mechanistic studies of the cyclopropanation of a series of trans-stilbenes by ethyl diazoacetate catalyzed by two different triarylaminium salts decisively confirm a cation radical mechanism and rule out a hypothetical electrophilic mechanism. The elucidation of key aspects of these cation radical mechanisms, including kinetic vs equilibrium control of ionization and chain vs catalytic mechanisms, has also been achieved for these systems. New mechanistic criteria for the positive identification of cation radical mechanisms are proposed.
Ultrasound-Mediated Synthesis and Mass Spectrometric Fragmentation of Dimethyl-Substituted 1,2-Diphenylethanols, Convenient Dimethylstilbene Precursors
Burkow, Ivan C.,Sydnes, Leiv K.,Ubeda, Danielle C. N.
, p. 235 - 244 (2007/10/02)
1,2-Diarylethanols were obtained in high yields by ultrasonic irradiation of mixtures of lithium sand, benzylic chlorides, and arenecarbaldehydes or aryl methyl ketones.The mass spectra of the alcohols contained dominant peaks for species formed by dehydration, α-cleavage processes and rearrangement involving hydrogen transfer.Acid-catalyzed dehydration of the alcohols gave the corresponding stilbenes in quantitative yields.
Photochemical Oxidation of Toluene and Xylenes. Concurrent Formation of Products Due To Photooxygenation and Photodimerization
Sydnes, Leiv K.,Burkov, Ivan C.,Hansen,Sissel H.
, p. 829 - 836 (2007/10/02)
Irradiation throuh pyrex of toluene and o-, m- and p-xylene in the liquid phase in the presence of air gave product mixtures which mainly contained alcohols, aldehydes, acids, and various dimers.
Carbon-Hydrogen vs. Carbon-Carbon Bond Cleavage of 1,2-Diarylethane Radical Cations in Acetonitrile-Water
Camaioni, Donald M.,Franz, James A.
, p. 1607 - 1613 (2007/10/02)
Radical cations of 1,2-diarylethanes and 1-phenyl-2-arylethanes (Ar = phenyl, p-tolyl, p-anisyl) were generated in acidic 70percent acetonitrile-water by Cu2+-catalyzed peroxydisulfate oxidation.The radical cations fragment mainly by loss of benzylic protons (C-H cleavage) rather than by alkyl C-C bond cleavage.The radical cation of 2,3-dimethyl-2,3-diphenylbutane fragments efficiently by C-C cleavage, forming cumyl radical and cumyl cation.Oxidations of bibenzyl-bicumyl mixtures show selective oxidation of bicumyl dependent on total substrate concentration, providing evidence of equilibrating radical cations and showing that bicumyl fragments faster than bibenzyl loses protons.The effects of reaction conditions and substrate structure on reactivity are discussed.
