74592-04-4

Upstream product

• 5428-09-1 3-phthalimido-1-propene 
• 100-44-7 benzyl chloride 
• 25316-59-0 benzyl tri-n-butylammonium bromide 
• 1074-82-4 potassium phtalimide 
• 591-50-4 iodobenzene 
• 52898-32-5 N-(3-butenyl)phthalimide 
• 7515-41-5 (E)-(4-bromobut-1-en-1-yl)benzene 
• 7743-29-5 [3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-triphenyl-phosphonium bromide 
• 100-52-7 benzaldehyde 

Downstream Products

• 54981-87-2 2-(4-phenylbutyl)-1H-isoindole-1,3(2H)-dione 
• 189098-54-2 2-[2-(2-Phenyl-cyclopropyl)-ethyl]-isoindole-1,3-dione 
• 24517-59-7 2-phenyl-1-(4-methylbenzenesulfonyl)pyrrolidine 
• 39551-07-0 (E)-4-methyl-N-(4-phenylbut-3-en-1-yl)benzenesulfonamide 
• 106814-09-9 N-(E)-(4-phenylbut-3-en-1-yl)acetamide 
• 7515-38-0 (E)-4-phenylbut-3-en-1-amine 

Relevant academic research and scientific papers

Vinylation of alkyl halides catalyzed by palladium catalyst

The palladium catalyzed vinylation of alkyl halides, especially benzyl chlorides, with a variety of olefins has been studied. A possible free radical mechanism was proposed.

Tuning the Selectivity of Palladium Catalysts for Hydroformylation and Semihydrogenation of Alkynes: Experimental and Mechanistic Studies

Here, we describe a selective palladium catalyst system for chemodivergent functionalization of alkynes with syngas. In the presence of an advanced ligand L2 bearing 2-pyridyl substituent as a built-in base, either hydroformylation or semihydrogenation of diverse alkynes occurs with high chemo- and stereoselectivity under comparable conditions. Mechanistic studies, including density functional theory (DFT) calculations, kinetic analysis, and control experiments, revealed that the strength and concentration of acidic cocatalysts play a decisive role in controlling the chemoselectivity. DFT studies disclosed that ligand L2 not only promotes heterolytic activation of hydrogen similar to frustrated Lewis pair (FLP) systems in the hydrogenolysis step for hydroformylation but also suppresses CO coordination to promote semihydrogenation under strong acid conditions. This switchable selectivity provides a strategy to design new catalysts for desired products.

Alkene Oxyamination Using Malonoyl Peroxides: Preparation of Pyrrolidines and Isoxazolidines

Treatment of homoallylic N-tosyl amines or allylic N-tosyl hydroxylamines with 1.5 equiv of a malonoyl peroxide provides a stereoselective method to access functionalized pyrrolidines and isoxazolidines. This metal free alkene oxyamination proceeds in 50-

Synthetic efforts toward the Lycopodium alkaloids inspires a hydrogen iodide mediated method for the hydroamination and hydroetherification of olefins

Progress toward the total syntheses of a diverse set of fawcettimine-type Lycopodium alkaloids via a "Heathcock-type" 6-5-9 tricycle is disclosed. This route features an intermolecular Diels-Alder cycloaddition to rapidly furnish the 6-5-fused bicycle and a highly chemoselective directed hydrogenation to build the azonane fragment. While conducting these synthetic studies, trimethylsilyl iodide was found to effect a hydroamination reaction to furnish the tetracyclic core of serratine and related natural products. This observation has been expanded into a general method for the room temperature hydroamination of unactivated olefins with tosylamides utilizing catalytic "anhydrous" HI (generated in situ from trimethylsilyl iodide and water). The presence of the iodide anion is critical to the success of this Bronsted acid catalyzed protocol, possibly due to its function as a weakly coordinating anion. These conditions also effect the analogous hydroetherification reaction of alcohols with unactivated olefins.

Convenient route to primary (Z)-allyl amines and homologs

A convenient two-step procedure for the synthesis of primary (Z)-allyl amines, (Z)-homoallyl amines [(Z)-but-3-enylamines], and (Z)-pent-4-enylamines using the Wittig reaction was achieved. The use of nonstabilized ylides from triphenylphosphonium salt, potassium salt, and apolar solvent produced (Z/E)-geometric isomer ratios generally greater than 1.6. The amine moiety was masked using a phtalimide group that was removed successfully in the last step of the process in two different conditions, NH2NH2/EtOH/rt or CH3NH2/EtOH/rt. However, in some cases, reduction of the C = C double bond in the deprotection with hydrazine was concomitantly observed. Copyright Taylor & Francis Group, LLC.

The intramolecular electron transfer reactions of N-Alkylcyclopropyl phthalimides

N-Alkylcyclopropyl phthalimides 5 and 6 were photolyzed to afford spiro lactams 17, 18 and 20-24. These products arise via an intramolecular electron transfer reaction between the phthalimide and the phenylcyclopropane portions of the molecule. The result

Vinylation of benzylic quaternary ammonium salts catalyzed by palladium

The palladium-catalyzed vinylation of benzylic tributylammonium salts with a variety of olefins has been studied. A possible free radical mechanism is proposed.