70303-26-3Relevant academic research and scientific papers
Iron Catalyzed Isomerization of α-Alkyl Styrenes to Access Trisubstituted Alkenes
Xu, Songgen,Liu, Guixia,Huang, Zheng
, p. 585 - 589 (2021/02/01)
Stereoselective isomerization of α-alkyl styrenes is accomplished using a new iron catalyst supported by phosphine-pyridine-oxazoline (PPO) ligand. The protocol provides an atom-efficient and operationally simple approach to trisubstituted alkenes in high
Highly Stereoselective Positional Isomerization of Styrenes via Acid-Catalyzed Carbocation Mechanism
Hu, Xiao-Si,He, Jun-Xiong,Zhang, Ying,Zhou, Jian,Yu, Jin-Sheng
supporting information, p. 2227 - 2233 (2021/06/28)
The first transition metal-free highly stereoselective positional isomerization of various α-alkyl styrenes through a carbocation mechanism triggered strategy is developed by using Al(OTf)3 as a hidden Br?nsted acid catalyst, which provides facile access to value-added acyclic tri- and tetra-substituted alkenes in good yields with high stereoselectivity under mild conditions. The practicality of this protocol is further highlighted by the gram-scale synthesis, high stereoselectivity, good functional group tolerance, and simple operation. Mechanistic studies support that Al(OTf)3 acts as a hidden Br?nsted acid catalyst and a carbocation intermediate is formed.
Stereoretentive Pd-catalyzed kumada-corriu couplings of alkenyl halides at room temperature
Krasovskiy, Arkady L.,Haley, Stephen,Voigtritter, Karl,Lipshutz, Bruce H.
supporting information, p. 4066 - 4069 (2014/10/15)
Stereoselective palladium-catalyzed Kumada-Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, including those bearing β-hydrogen atoms and sensitive functional groups, can be carried out at room temperature using a new combination of reagents.
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.
Sulfoxide-modified Julia-Lythgoe olefination: Highly stereoselective di-, tri-, and tetrasubstituted double bond formation
Pospisil, Jiri,Pospisil, Tomas,Marko, Istvan E.
, p. 1953 - 1969 (2007/10/03)
A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and SmI 2/HMPA or SmI2/DMPU-mediated reductive elimination, 1,2-di-, tri- and tetrasubstituted olefins in moderate to good yields and E/Z selectivity. The conditions are mild and the procedure is widely applicable. The reaction mechanism was studied and a general model, describing the reaction selectivity, is proposed.
Sulfoxides in Julia-Lythgoe olefination: Efficient and stereoselective preparation of di-, tri-, and tetrasubstituted olefins
Pospisil, Jiri,Pospisil, Tomas,Marko, Istvan E.
, p. 2373 - 2376 (2007/10/03)
(Chemical Equation Presented) A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and Sml2/HMPA- or DMPU-mediated reductive elimination, 1,2-di-, tri-, and tetrasubstituted olefins in moderate to excellent yields and E/Z selectivity. The conditions are mild, and the procedure is broadly applicable.
A Convergent Method for the Stereoselective Synthesis of Trisubstituted Alkenes
Martin, Stephen F.,Daniel, Dilon,Cherney, Robert J.,Liras, Spiros
, p. 2523 - 2525 (2007/10/02)
A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed.The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent.Treatment of 9 with carbon disulfide
Formylation and Acylation Reactions Catalysed by Trifluoromethanesulphonic Acid
Booth, Brian L.,El-Fekky, Teymour A.,Noori, Ghazi F. M.
, p. 181 - 186 (2007/10/02)
Regioselective formylation of toluene, m- and p-xylene, and mesitylene has been achieved by carbonylation in trifluoromethanesulphonic acid at CO pressures of 90-125 atm.In the case of cumene, the formylation reaction is in competition with disproportionation to form di- and tri-isopropylbenzenes, leading to a complex product mixture.Slow addition of cyclohexene or cyclopentene to a mixture of benzene and CF3SO3H under a high CO pressure affords 4-cyclohexylbenzaldehyde and 4-cyclopentylbenzaldehyde in 34percent and 33percent yieds, respectively, while 2-methylbut-1-ene gives 2,2,3-trimethylindanone (39percent) under similar conditions.When cyclohexene is mixed with the acid under carbon monoxide (120 atm) before addition of benzene the major products are cyclohexyl phenyl ketone and cyclohexenyl cyclohexyl ketones.
