93014-82-5

Upstream product

• 35258-38-9 rac-1-(4-methoxyphenyl)-2-phenylpropan-1-one 
• 25145-43-1 2-phenylpropionyl chloride 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 90875-08-4 (rac)-4-(2-bromopropyl)-1-methoxybenzene 
• 199168-44-0 (rac)-1-methoxy-4-[2-(phenylthio)propyl]benzene 
• 1239477-82-7 (rac)-1-methoxy-4-[2-(phenylsulfonyl)propyl]benzene 
• 100-58-3 phenylmagnesium bromide 
• 696-62-8 para-iodoanisole 
• 98-83-9 isopropenylbenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 121213-48-7 9-(2-phenylpropyl)-9-BBN 
• 824-94-2 p-methoxybenzyl chloride 
• 32970-78-8 2-phenyl-3-(4-methoxyphenyl)-propylnitrile 
• 857226-38-1 3-(4-methoxyphenyl)-2-methyl-2-phenylpropanenitrile 

Relevant academic research and scientific papers

"bulky-Yet-Flexible" α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air

To pursue a highly regioselective and efficient reductive Heck reaction, a series of moisture-and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the"bulky-yet-flexible"palladium complexes allowed highly anti-Markovnikov-selective hydroarylation of alkenes with (hetero)aryl bromides under aerobic conditions. Further synthetic application of the present protocol could provide rapid and straightforward access to functional and biologically active molecules.

Nickel-catalyzed anti-Markovnikov hydroarylation of alkenes

We have developed a nickel-catalyzed hydroarylation of alkenes using aryl halides as coupling partners. Excellent anti-Markovnikov selectivity is achieved with aryl-substituted alkenes and enol ethers. We also show that hydroarylation occurs with alkyl substituted alkenes to yield linear products. Preliminary examination of the reaction mechanism suggests irreversible hydrometallation as the selectivity determining step of the hydroarylation.

Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study

The rearrangement of sulfamoyl azides under thermal conditions to form a C-C bond while breaking two C-N bonds is reported. Mechanistic study shows that this reaction goes through a Curtius-type rearrangement to form a 1,1-diazene, then which rearranges possibly through both a concerted rearrangement process and a stepwise radical process. This rearrangement could be used in the synthesis of complex biologically active molecules, such as sterols, and piperine derivatives.

The copper-catalysed Suzuki-Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation

We report the first example of CuI-catalysed coupling of alkylboron reagents with aryl and heteroaryl iodides that affords products in good to excellent yields. Preliminary mechanistic studies with alkylborates indicate that the anionic (alkoxy)(alkyl)borates, generated from alkyllithium and alkoxyboron reagents, undergo disproportionation to anionic dialkylborates and that both anionic alkylborates are active for transmetalation to a CuI-catalyst. Results from a radical clock experiment and the Hammett plot imply that the reaction likely proceeds via a non-radical pathway.

Hydride Reduction by a Sodium Hydride-Iodide Composite

Sodium hydride (NaH) is widely used as a Br?nsted base in chemical synthesis and reacts with various Br?nsted acids, whereas it rarely behaves as a reducing reagent through delivery of the hydride to polar π electrophiles. This study presents a series of reduction reactions of nitriles, amides, and imines as enabled by NaH in the presence of LiI or NaI. This remarkably simple protocol endows NaH with unprecedented and unique hydride-donor chemical reactivity.

Cross-coupling of nonactivated primary and secondary alkyl halides with aryl Grignard reagents catalyzed by chiral iron pincer complexes

Iron(III) bisoxazolinylphenylamido (bopa) pincer complexes are efficient precatalysts for the cross-coupling of nonactivated primary and secondary alkyl halides with phenyl Grignard reagents. The reactions proceed at room temperature in moderate to excellent yields. A variety of functional groups can be tolerated. The enantioselectivity of the coupling of secondary alkyl halides is low.

Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl grignard reagents

The first systematic investigation of unactivated aliphatic sulfur compounds as electrophiles in transition-metal-catalyzed cross-coupling are described. Initial studies focused on discerning the structural and electronic features of the organosulfur substrate that enable the challenging oxidative addition to the C(sp3)-S bond. Through extensive optimization efforts, an Fe(acac)3-catalyzed cross-coupling of unactivated alkyl aryl thio ethers with aryl Grignard reagents was realized in which a nitrogen "directing group" on the S-aryl moiety of the thio ether served a critical role in facilitating the oxidative addition step. In addition, alkyl phenyl sulfones were found to be effective electrophiles in the Fe(acac) 3-catalyzed cross-coupling with aryl Grignard reagents. For the latter class of electrophile, a thorough assessment of the various reaction parameters revealed a dramatic enhancement in reaction efficiency with an excess of TMEDA (8.0 equiv). The optimized reaction protocol was used to evaluate the scope of the method with respect to both the organomagnesium nucleophile and sulfone electrophile.

Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium

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.

Helical twisting power of new chiral dopants derived from 2-phenylpropanoic acid for nematic liquid crystals

New chiral dopants for nematic liquid crystals were synthesized using optically active 2-phenylpropanoic acid. The magnitude of helical twisting power (HTP) was largely influenced by the linkages between the asymmetric frame and the core moieties. The results of our experiments clearly showed that a steric effect was important to induce a helical macrostructure.