37549-95-4

Upstream product

• 109182-89-0 1-phenyl-1,2-pentadiene 
• 616-25-1 1-Penten-3-ol 
• 71-43-2 benzene 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 73654-55-4 (E)-1-(Triethylsilyl)-3-phenyl-1-propen-3-ol 
• 849518-46-3 1-phenyl-3-(triethylsilyl)prop-2-yn-1-ol 
• 4173-48-2 (1-((2-methoxypropan-2-yl)oxy)prop-2-yn-1-yl)benzene 
• 676-58-4 methylmagnesium chloride 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 122-78-1 phenylacetaldehyde 
• 123-72-8 butyraldehyde 
• 925-90-6 ethylmagnesium bromide 
• 41796-48-9 ((Z)-3-Ethylsulfanyl-allyl)-benzene 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

Palladium-catalyzed reaction of γ-silylated allyl acetates proceeding through 1,2-shift of a substituent on silicon

The palladium-catalyzed reaction of γ-silylated allyl acetates with water in the presence of CsF induces a previously unprecedented 1,2-shift of a substituent on silicon to produce allylsilanes in situ. The catalytic activity of the palladium increased when using an electron-poor phosphine ligand possessing fluorinated substituents. Further investigation of the reaction revealed that the approximate order of the migratory aptitude of groups from silicon was PhC≡C, allyl > Bn > Ph, vinyl > alkyl (Me, Et). A density functional theory study was employed to explore the reaction mechanism. Finally, the Hosomi–Sakurai-type allylation of aldehydes with in situ-generated α,γ-disubstituted allylsilanes was also investigated.

Use of the 2-Pyridinesulfonyloxy Leaving Group for the Fast Copper-Catalyzed Coupling Reaction at Secondary Alkyl Carbons with Grignard Reagents

Investigation of the copper-catalyzed coupling reaction of 2-pyridinesulfonates with Grignard reagents revealed that reactions with catalytic Cu(OTf)2 were completed in 40 min. The results differed from those of the previous CuI-catalyzed reactions of tosylates in the presence of additives (LiOMe and TMEDA) for 12-24 h. It was shown that the preferred coordination of the leaving group to the reagents accelerated the reaction. Successful reagents were MeMgCl and other RMgX. Complete inversion was established.

Alkene isomerization-hydroarylation tandem catalysis: Indole c2-alkylation with aryl-substituted alkenes leading to 1,1-diarylalkanes

A cobalt-N-heterocyclic carbene catalyst generated from CoBr2, imidazolium salt, and cyclohexylmagnesium bromide was found to promote the imine-directed C2-alkylation of indoles with nonconjugated arylalkenes through a tandem alkene isomerization-hydroarylation process, affording 1,1-diarylalkanes with exclusive regioselectivity. The feasibility of the tandem catalysis was demonstrated for allyl-, homoallyl-, and bishomoallylbenzene derivatives. The catalytic system is also applicable to a variety of β-substituted styrene derivatives. Mechanistic experiments using deuterium-labeled indole substrate and Grignard reagent provided insight into the cobalt-mediated C -H activation step, which likely involves exchange of the C2-hydrogen atom of the former and the β-hydrogen atoms of the latter. ...? but thats secondary: A catalytic system consisting of CoBr2, N-heterocyclic carbene, and cyclohexylmagnesium bromide promotes the imine-directed addition of indoles to nonconjugated aryl-substituted alkenes through tandem alkene isomerization-hydroarylation, affording 1,1-diarylalkane derivatives with exclusive regioselectivity. Deuterium-labeling experiments revealed the involvement of the secondary alkyl Grignard reagent in the cobalt-mediated C -H activation process.

Reactions of polymer-supported α-selenoaldehydes with Grignard regents. A facile solid-phase stereoselective synthesis of (E)-1,2-disubstituted ethenes

Polymer-supported α-selenoaldehydes easily obtained by reaction of polymer-supported 4-(phenyl-seleno)morpholine with aldehydes react with Grignard reagents to form polymer-supported β-hydroxyalkyl selenides, which were treated with thionyl chloride/triethylamine leading to (E)-1,2-disubstituted ethenes in good yields.

Scandium(III) Triflate-Catalyzed Friedel-Crafts Alkylation Reactions

The Sc(OTf)3-catalyzed Friedel-Crafts alkylation reaction with an alcohol, an arenecarbaldehyde or an arenecarbaldehyde acetal as the alkylating agent affords a diarylmethane or an allylbenzene derivative highly selectively. The salient feature of this reaction is that only a catalytic amount of Sc(OTf)3 can effect the reaction. Furthermore, Sc(OTf)3 is recoverable and reusable after the synthetic reaction. The Sc(OTf)3-catalyzed benzylation using an arenecarbaldehyde and 1,3-propanediol or their acetal affords diarylmethane as a sole product in excellent yields in sharp contrast to the original Friedel-Crafts reaction. Since no reaction occurs in the absence of 1,3-propanediol, the reaction is considered to proceed through a redox process including a hydride shift. The hydride shift mechanism is strongly supported by the experimental evidence. The reaction of benzaldehyde with benzene in the presence of 1,3-propanediol-1,1,3,3,-d4 gives rise to the deuterium incorporation into the benzylic carbon of diphenylmethane. Worthy of note is that 1,3-propanediol acts as the hydride source. Herein, diphenylmethyl 3-hydroxypropyl ether is assumed to be the most likely intermediate. In this reaction, Sc(OTf)3 catalyst effectively promotes initial acetal formation, electrophilic aromatic substitution, and successive intramolecular hydride transfer.

A General Olefin Synthesis

The reaction between secondary Grignard reagents and alkylthioarenes or alkylthioalkenes in the presence of 1:1 nickel dichloride-triphenylphosphine causing the substitution of alkylthio-groups by hydrogen atoms, the nickel(0)-induced replacement of alkylthio-groups of the aforementioned sulfides by alkyl or aryl functions, and the observation of regiocontrol in the catalysed reactions of Grignard reagents with unsymmetrical 1,1-bis(alkylthio)alkenes have led to a scheme of general, regio-, and stereo-selective olefin synthesis.

Effects of Phenyl and Alkyl Substitutions on the Hydrogenation of Allene with Diimide

Hydrogenation of phenylpropadiene, 3-phenyl-1,2-butadiene, 1-phenyl-1,2-butadiene, and 1-phenyl-1,2-pentadiene with diimide (HN=NH) in refluxing methanol was conducted.The product distribution was analyzed as a function of reaction time, and the selectivities of the addition as well as relative reactivities were determined.Adverse steric effects of the phenyl group at the terminus of one double bond against "cis-coplanar" attack of diimide on the other double bond were found to be remarkably large.Alkyl groups activated the remote double bond of alkylallenes noticeably.This apparent electronic effect was theoretically rationalized from ab initio STO-3G model calculations of the chemical interactions.