63413-74-1

Usage

Structure

1H-Isoindole-1,3(2H)-dione, 2-[(4-ethenylphenyl)methyl]-

Derivative

Phthalimide derivative

Contains

A vinyl group attached to a phenyl ring

Usage

Organic synthesis as a starting material for the preparation of various substances, including pharmaceuticals and agrochemicals

Potential

Demonstrated potential biological activity and is being studied for its pharmacological properties

Also used as

A reagent in chemical reactions, such as the synthesis of various organic compounds and polymers.

Upstream product

• 136918-14-4 phthalimide 
• 1592-20-7 4-Vinylbenzyl chloride 
• 73291-09-5 4-chloromethylbenzaldehyde 
• 51359-79-6 4-((1,3-dioxoisoindolin-2-yl)methyl)benzaldehyde 
• 19493-09-5 Methylenetriphenylphosphorane 
• 1074-82-4 potassium phtalimide 

Downstream Products

• 50325-49-0 p-vinylbenzylamine 

Relevant academic research and scientific papers

Transition metal-free formal hydro/deuteromethylthiolation of unactivated alkenes

Methylthioether is involved in the methylthiotransfer process in organisms, and therefore its functionality is of paramount importance to living organisms. Several methods for the installation of the methylthio group in small molecules have been reported previously; however, procedures starting from unactivated alkenes are rare. Herein, we report a formal hydro/deuteromethylthiolation of alkenes by using dimethyl(methylthio)sulfonium trifluoromethanesulfonate as the stimulator and sodium borohydride/deuteride as the hydrogen/deuterium source. The process represents a mild, transition metal-free and methanethiol-free route towards the synthesis of methylthioethers from unactivated alkenes. This journal is

Visible-Light-Induced Pd-Catalyzed Radical Strategy for Constructing C-Vinyl Glycosides

A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochemistry selectivity for the preparation of C-glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved.

Physically mixed catalytic system of amino and sulfo-functional porous organic polymers as efficiently synergistic co-catalysts for one-pot cascade reactions

In this article, acid/base bi-functional polymeric materials were prepared using physically mixed porous poly(divinylbenzene-co-4-vinylbenzenesulfonic acid) (P(DVB-VBS)) with sulfonic acid groups and poly(divinylbenzene-co-4-vinylbenzyl amine) (P(DVB-VBA)) with amino groups, which were synthesized by solvothermal polymerization of crosslinker DVB with either phenyl 4-vinylbenzenesulfonate (PVBS) or 4-vinylbenzyl amine hydrochloride (VBAH) functional monomers together with subsequent hydrolyzation or alkaline treatment. The bi-functional polymeric materials were utilized as a synergistic catalytic system for one-pot cascade reactions including deacetalization-Henry condensation reaction, deacetalization-Knoevenagel condensation reaction and the transformation of 3,4-dihydropyran derivatives to α-ester cyclohexenone compounds. The crosslinked polymeric frameworks effectively isolated sulfonic acid and primary amine groups to ensure their roles as both acid and base catalyst simultaneously in a one-pot system. The hierarchical porosity of a physically mixed acid/base co-catalyst system provided the possibility for the multi-step transformation of more complex substrates.

Overcoming Selectivity Issues in Reversible Catalysis: A Transfer Hydrocyanation Exhibiting High Kinetic Control

Reversible catalytic reactions operate under thermodynamic control, and thus, establishing a selective catalytic system poses a considerable challenge. Herein, we report a reversible transfer hydrocyanation protocol that exhibits high selectivity for the thermodynamically less favorable branched isomer. Selectivity is achieved by exploiting the lower barrier for C-CN oxidative addition and reductive elimination at benzylic positions in the absence of a cocatalytic Lewis acid. Through the design of a novel type of HCN donor, a practical, branched-selective, HCN-free transfer hydrocyanation was realized. The synthetically useful resolution of a mixture of branched and linear nitrile isomers was also demonstrated to underline the value of reversible and selective transfer reactions. In a broader context, this work demonstrates that high kinetic selectivity can be achieved in reversible transfer reactions, thus opening new horizons for their synthetic applications.

Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature

It is reported that Pd(PPh3)2Cl2 in combination with 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) under irradiation of blue LEDs efficiently catalyzes a decarboxylative Heck reaction of vinyl arenes and vinyl heteroarenes with aliphatic N-(acyloxy)phthalimides at room temperature. A broad scope of secondary, tertiary, and quaternary carboxylates, including α-amino acid derived esters, can be applied as amenable substrates with high stereoselectivity. The experimental observation was explained by excitation-state reactivity of the palladium complex under irradiation to induce single-electron transfer to activate N-(acyloxy)phthalimides, and to suppress undesired β-hydride elimination of alkyl palladium intermediates.

Heteroatom Donor-Decorated Polymer-Immobilized Ionic Liquid Stabilized Palladium Nanoparticles: Efficient Catalysts for Room-Temperature Suzuki-Miyaura Cross-Coupling in Aqueous Media

Palladium nanoparticles stabilized by heteroatom donor-modified polystyrene-based polymer immobilized ionic liquids (PdNP@HAD-PIILP; HAD-PPh2, OMe, NH2, CN, pyrrolidone) are highly efficient catalysts for the Suzuki-Miyaura cross-cou

Surface glycopolymer-modified functional macroporous polyHIPE obtained by ATRP for the removal of boron in water

Amino-functional macroporous polyHIPE-NH2 monoliths were surface modified with 2-bromo-2-methylpropionyl bromide and used as initiators to initiate atom transfer radical polymerization (ATRP) of the d-gluconamidoethyl methacrylate glycol-monome

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature

The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination.

Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions

Molecular structures of the most prominent chiral non-racemic hypervalent iodine(III) reagents to date have been elucidated for the first time. The formation of a chirally induced supramolecular scaffold based on a selective hydrogen-bonding arrangement provides an explanation for the consistently high asymmetric induction with these reagents. As an exploratory example, their scope as chiral catalysts was extended to the enantioselective dioxygenation of alkenes. A series of terminal styrenes are converted into the corresponding vicinal diacetoxylation products under mild conditions and provide the proof of principle for a truly intermolecular asymmetric alkene oxidation under iodine(I/III) catalysis.