56074-64-7Relevant academic research and scientific papers
Reductive cross-coupling between N-acylbenzimidazoles and diarylketones promoted by Sm/TiCl4
Du, Jingxing,Wang, Xiaoxia,Zheng, Renwei
, p. 14 - 15 (2007/10/03)
The reductive cross-coupling reaction between N-acylbenzimidazoles and diarylketones promoted by Sm/TiCl4 was performed in refluxing THF under a nitrogen atmosphere, to give 1,2,2-triaryl ethanones in moderate to good yields.
Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: An example of a heck triarylation process
Nilsson,Larhed,Hallberg
, p. 8217 - 8225 (2007/10/03)
This article describes the development of new auxiliary-accelerated Heck multiarylations by intramolecular presentation of the oxidative addition complex. The introduction of a specific, palladium-coordinating dimethylamino group allows for the desired chelation-accelerated and chelation-controlled tri- and diarylation reactions. We report (a) the first example of a Heck triarylation process, (b) highly selective palladium-catalyzed diarylations of alkyl vinyl ethers, and (c) a very rapid two-phase protocol for the microwave-assisted hydrolysis of amino-substituted, arylated vinyl ethers constituting an entry to diarylated ethanals and substituted desoxybenzoins. X-ray structures and product patterns support the suggested substrate-controlled Heck reaction pathway. The catalyst-directing alkyl dimethylamino functionality was rapidly (1-2 min) and efficiently released by microwave hydrolysis after Heck multiarylation reactions. The liberated aromatic carbonyl compounds were thereafter isolated and fully characterized.
Novel Deoxygenative Acylation of Diaryl Ketones with Acylsilanes Mediated by Lanthanoid Metals
Taniguchi, Yuki,Nagafuji, Akihiro,Makioka, Yoshikazu,Takaki, Ken,Fujiwara, Yuzo
, p. 6897 - 6898 (2007/10/02)
The reaction of diaryl ketones and benzoyltrimethylsilane is mediated by lanthanoid metals such as ytterbium to give the deoxygenatively acylated product, 1,1-diarylacetophenones in good yields.In the reaction with acetylsilane, the corresponding silyl enol ether was obtained in a moderate yield.
Radical ions in photochemistry. Carbon-carbon bond cleavage of radical cations in solution: Theory and application
Popielarz,Arnold
, p. 3068 - 3082 (2007/10/02)
The cleavage of radical cations of two series of alkanes, 1,1,2-triaryl- and 1,1,2,2-tetraarylalkanes, generated by photoinduced single electron transfer in acetonitrile-methanol, occurs with formation of radical and carbocation fragments. The radical cations of some unsymmetrically substituted alkanes cleave to give all four of the possible products, two hydrocarbons emanating from the radicals and two methyl ethers from the carbocations, in proportion to the oxidation potentials of the two possible radical fragments. There is an excellent linear correlation between the logarithm of the observed ratio of products and that calculated from the reported electrochemically determined oxidation potentials (r = 0.998, 5 points). The proportionality constant (1.27) for this relationship is close to unity which indicates that the product ratio is determined by the relative rates of cleavage in the two possible modes or by equilibration of the radicals and carbocations before separation of the geminate radical carbocation pair and not by equilibration upon reencounter of freely solvated radical and carbocation fragments. The effect of temperature on the relative oxidation potentials of the radicals studied is small and can be neglected when radicals of the same order (i.e., both secondary or both tertiary) and of similar size are compared. The ratio of products obtained upon cleavage of the radical cation at 25 °C can be used to determined standard oxidation potentials of radicals. The oxidation potential of the diphenylmethyl radical (0.350 V vs SCE) has been accepted as the primary standard and the (4-methyl-phenyl)phenylmethyl (0.265 V) and bis(4-methylphenyl)methyl (0.188 V) radicals are established as secondary standards against which the oxidation potentials of other radicals can be measured. Oxidation potentials of several 4-substituted cumyl radicals have been determined by this photochemical method. There is a good (r = 0.987, 5 points) linear correlation between the measured oxidation potentials and the σ+ substituent constants. The reaction constant is appropriately negative and large (p = -6).
