356782-30-4

Upstream product

• 1866-39-3 trans-p-methylcinnamic acid 
• 71-43-2 benzene 
• 108-88-3 toluene 
• 4192-77-2 ethyl cinnamate 
• 100-52-7 benzaldehyde 
• 1610735-49-3 2-ethynyl-1-(methoxy(phenyl)methyl)-4-methylbenzene 
• 4360-47-8 cinnamonitrile 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 99-04-7 m-Toluic acid 

Downstream Products

• 88-99-3 benzene-1,2-dicarboxylic acid 

Relevant academic research and scientific papers

Iridium-Catalyzed Synthesis of Substituted Indanones from Aromatic Carboxylates and Unsaturated Ketones

A catalytic annulation is presented that provides straightforward, modular synthetic access to 3-substituted indanones from benzoic acids and α,β-unsaturated ketones. It is catalyzed by a bimetallic Ir/In system and proceeds via hydroarylation followed by

Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid

The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH2CN] and/or 3-phenylindanones in 28–76% yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group.

Gold-catalyzed carboalkoxylations of 2-ethynylbenzyl ethers to form 1- and 2-indanones chemoselectively: Effects of ligands and solvents

The selective syntheses of 1- and 2-indan-one compounds from 2-ethynylbenzyl ethers have been achieved with suitable catalysts and solvents. The highly acidic [tris(pentafluorophenyl)phos-phine]gold hexafluoroantimonate [(C6F5)3AuSbF6] in nitromethane (MeNO2) preferably gives 1-indan-ones whereas [(ortho-biphenyl) di(tert-butyl)phosphine] gold triflimide [(tBu)2(o-biphenyl) AuNTf2] in dichloroethane tends to form 2-indanone derivatives. For 2-indanone products, we isolated two indenyl methyl ethers for deuterium labeling analyses, providing evidence for p-alkyne activation.

Electronic effects of substituents on the stability of the iridanaphthalene compound [IrCp{C(OMe)CHC(o-C6H4)(Ph)}(PMe3)]PF6

Iridanaphthalene complexes are synthesized from the corresponding methoxy(alkenyl)carbeneiridium compounds. The electronic character of the substituents on the 6-position of the metallanaphthalene ring is crucial from the point of view of the stability of the iridanaphthalene, [IrCp{C(OMe)CHC(o-C6H4)(Ph)}(PMe3)]PF6, vs. its transformation to the corresponding indanone derivatives. Stability studies of the iridanaphthalene compounds revealed that strong electron donor substituents (-OMe) stabilize the iridanaphthalene, while weak electron donor (-Me) and electron withdrawing (-NO2) groups favor the formation of indanone derivatives. Two possible indanone isomers can be obtained in the conversion of the unstable iridanaphthalene complexes and a mechanism for the formation of these isomers is proposed. This journal is

Superacid-promoted dual C-C bond formation by Friedel-Crafts alkylation and acylation of ethyl cinnamates: Synthesis of indanones

A superacid (triflic acid) promoted dual C-C bond formation via intermolecular Friedel-Crafts alkylation (Michael addition type) and intramolecular acylation for the efficient synthesis of 3-substituted indan-1-ones is presented. This method was successful in activating ethyl cinnamates towards dual aromatic electrophilic substitution. Moreover, it enabled us to synthesize novel spirotetracyclic systems. Georg Thieme Verlag Stuttgart · New York.

Superacid-Catalyzed Reactions of Cinnamic Acids and the Role of Superelectrophiles

The chemistry of cinnamic acids and related compounds has been studied. In superacid-catalyzed reactions with arenes, two competing reaction mechanisms are proposed. Both mechanisms involve the formation of dicationic intermediates (superelectrophiles), and the reactions can lead to either chalcone-type products or indanone products. The direct observation of a dicationic species (by low-temperature 13C NMR) is reported. We provide clear evidence that protonated carboxylic acid groups (or the corresponding acyl cation) can enhance the reactivity of an adjacent electrophilic center. Triflic acid is also found to be an effective acid catalyst for the direct synthesis of some electron-deficient chalcones and heterocyclic chalcones from cinnnamic acids.