78525-36-7Relevant academic research and scientific papers
Ultrasonic activation of the arylation reaction of styrene catalyzed by transition metals
Atoui, Dhiab,Sa?d, Khemais,Ben Salem, Ridha
, p. 587 - 600 (2017/09/18)
The arylation reaction of styrene was tested in the presence of different transition metal-based catalysts, mainly iron-based, given its low cost and its nonpolluting and nontoxic characteristics. The study of the effect of sonochemical activation on the evolution of the selectivity of the reaction is also proposed. Higher efficiency was observed for a very short period of time of just a few minutes. Furthermore, an improvement of the selectivity of the arylation of the external carbon of styrene was observed.
Phase-vanishing method applied to condensation reactions using TiCl4
Adachi, Yusuke,Kuniyoshi, Kenji,Matsubara, Hiroshi
, p. 100 - 105 (2017/04/10)
The phase-vanishing (PV) method using perfluorohexanes as the phase screen was applied to the aldol condensation using TiCl4 as the Lewis acid. A special test tube was used, in which an interface between the fluorous and organic layers was stirred, and cyclohexanone was treated with two equivalents of benzaldehyde derivatives under PV conditions to afford corresponding 2,6-dibenzylidencyclohexanone in good yields. The formyl-methylenation of ketones with triethylamine using TiCl4 was also demonstrated by the PV method.
One-pot synthesis of 1-iodoalkynes and trisubstituted alkenes from benzylic and allylic bromides
Pelletier, Guillaume,Lie, Sharon,Mousseau, James J.,Charette, Andre B.
, p. 5464 - 5467,4 (2020/10/15)
1-Iodoalkynes are formed in moderate to high yields from readily accessible benzylic and allylic alkyl bromides by a one-pot homologation/double elimination procedure with iodoform (CHI3). The developed conditions include facile purification and avoid the use of an excess of triphenylphosphine (PPh3), as described in classical Corey-Fuchs iodoalkynylation conditions. Replacing CHI3 with CHI2Cl allows the isolation of the corresponding gem-(Z)-chloro-(E)-iodoalkene in good yield and stereoselectivity. Moreover, the use of benzhydryl bromides as nucleophiles enables the synthesis of trisubstituted alkenes under similar reaction conditions.
Palladium/phosphite or phosphate catalyzed oxidative coupling of arylboronic acids with alkynes to produce 1,4-diaryl-1,3-butadienes
Horiguchi, Hakaru,Tsurugi, Hayato,Satoh, Tetsuya,Miura, Masahiro
supporting information; scheme or table, p. 509 - 514 (2009/04/10)
The intermolecular oxidative coupling of arylboronic acids with internal alkynes efficiently proceeds in a 2:2 manner in the presence of palladium acetate, a triaryl phosphite or phosphate, and silver carbonate as catalyst, ligand, and oxidant, respectively, to produce the corresponding 1,4-diaryl-1,3-butadiene derivatives.
Selenobenzophenones and diazoalkanes: Isolation of tetraarylethylenes by the reaction of benzophenone hydrazones with diselenium dibromide
Okuma, Kentaro,Kojima, Kazuki,Oyama, Kosuke,Kubo, Kento,Shioji, Kosei
, p. 820 - 825 (2007/10/03)
The reaction of selenobenzophenones with diazomethane afforded the corresponding diarylethylenes and symmetrical olefins. The reaction with diaryldiazomethanes gave three different types of tetraarylethylenes. This reaction proceeded through 1,3,4-selenadiazoline intermediates, and retrocyclization was observed. The formation of 1,3,4-selendiazolines was independently confirmed by the reaction of benzophenone hydrazones with diselenium dibromide, which afforded tetraarylethylenes in good yields. This method is applicable to the two-step synthesis of tetraarylethylenes from benzophenones. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Stereochemistry of the [4 + 2] cycloaddition of diarylselenoketones with conjugated dienes
Wilker, Stefanie,Erker, Gerhard
, p. 10922 - 10930 (2007/10/03)
The ylides Ph3P=CAr1Ar2 1a-g (Ar = C6H5, p-C6H4Cl, p-C6H4F, m-C6H4CF3, p-C6H4OCH3, p-C6H4-CH3) were treated with elemental selenium (～80°C) to give the corresponding selenoketones Se=CAr1Ar2 2 by Staudinger-chalcogenation. Their reaction with trans,trans-2,4-hexadiene proceeds completely stereospecifically to yield the 2,2-diaryl-3,6-dihydro-cis-3,6-dimethyl-2H-selenapyrans 3. In contrast, the reactions of the selenoketones 2 with cis,trans-2,4-hexadiene proceeds stereoselectively, also giving the dihydro-cis-dimethyl-2H-selenapyrans 3 as the major products, now admixed with small amounts of the dihydro-trans-dimethyl-2H-selenapyran isomers 4. The [4 + 2] cycloaddition of 2 with cis,trans-2,4-hexadiene proceeds stereospecifically, however, when carried out at a pressure of 12 kbar, now yielding 4 as the major products along with the corresponding tetraarylethenes 8. Along with the results of additional mechanistic studies (determination of solvent and substituent effects) it can be concluded that diarylselenoketones are likely to react by means of a concerted [4 + 2] cycloaddition with very reactive conjugated dienes (such as trans,trans-2,4-hexadiene), whereas a stepwise mechanism, resulting in diene cis/trans-isomerization with subsequent mechanistic "leakage" to the concerted pathway, appears to be preferred when a much less reactive conjugated diene such as cis,trans-2,4-hexadiene is employed. The reaction of the corresponding diarylthioketones 5a-g with trans,trans- and cis,trans-2,4-hexadiene, respectively, shows an analogous behavior.
FACILE CONVERSION, USING A VASTLY IMPROVED GATTERMAN PROCEDURE, OF ACTIVATED THIOBENZOPHENONES INTO TETRAARYLETHYLENES.
Baran, Janusz,Laszlo, Pierre
, p. 5135 - 5136 (2007/10/02)
A simple and inexpensive procedure is proposed for the title couplig, performed at room temperature in DMSO.
