84810-45-7

Upstream product

• 95-56-7 2-hydroxybromobenzene 
• 93-55-0 1-phenyl-propan-1-one 
• 533-58-4 2-Iodophenol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 84810-16-2 (1S,8S,9S)-1,8-Dimethyl-9-phenyl-10,11,12-trioxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene 
• 84847-62-1 (1S,8R,9S)-1,8-Dimethyl-9-phenyl-10,11,12-trioxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene 
• 84810-21-9 Acetic acid 2-(1-methyl-2-oxo-2-phenyl-ethyl)-phenyl ester 
• 84810-23-1 Benzoic acid 2-((Z)-2-hydroxy-1-methyl-2-phenyl-vinyl)-phenyl ester 
• 84810-20-8 Benzoic acid 2-(1-methyl-2-oxo-2-phenyl-ethyl)-phenyl ester 

Downstream Products

• 4521-08-8 3-methyl-2-phenylbenzofuran 

Relevant academic research and scientific papers

One-pot synthesis of benzofurans via palladium-catalyzed enolate arylation with o-bromophenols

(Chemical Equation Presented) A one-pot synthesis of benzofurans which utilizes a palladium-catalyzed enolate arylation is described. The process demonstrates broad substrate scope and provides differentially substituted benzofurans in moderate to excelle

Arylation of allyl alcohols in organic and aqueous media catalyzed by oxime-derived palladacycles: Synthesis of β-arylated carbonyl compounds

A 4-hydroxyacetophenone oxime-derived palladacycle catalyzes the Mizoroki-Heck reaction of allyl alcohols with aryl iodides, bromides, and chlorides in aqueous and organic solvents. The reaction takes place in the presence of dicyclohexylmethylamine or cesium carbonate as bases, the addition of tetrabutylammonium bromide (TBAB) as additive for aryl bromides and chlorides being necessary. Under these reaction conditions, β-arylated aldehydes and ketones are mainly obtained using a rather low loading of palladium (0.1-1 mol%). Similar catalytic activity is shown by a Kaiser oxime resin-derived palladacycle, which allows one to perform recycling and reusing experiments with low Pd leaching. The high regio- and chemoselectivity observed supported that these palladacycles, working as a source of Pd(0) species, operates mainly through a neutral mechanism. This methodology has been applied to the synthesis of important β-arylated carbonyl compounds, such as 4-phenylbutan-2-one, 4-(4-hydroxyphenyl)butan-2-one, dihydrochalcones, the anti-inflamatory nabumetone, and the fragance β-lilial. γ-Arylation is observed in the reactions of allyl alcohol and but-3-en-2-ol with 2-iodoaniline giving mainly the corresponding quinolines. The same tendency is observed in the case of 1,1-dimethylallyl alcohol affording either γ-arylated alcohols or (E)-1-arylisoprenes.

Synthesis, X-ray Analysis, and Acidolysis of exo- and endo-1-Methylindene Ozonides

Ozonolyses of 2,3-disubstituted 1-methylindenes gave mixtures of the corresponding exo and endo ozonides.The structures of endo-1-methyl-3-phenylindene ozonide (3a) and exo-1-methyl-2,3-diphenylindene ozonide (2b) were determined by the X-ray analysis.Acidolysis of exo- and endo-1-methylindene ozonides 2a-d and 3a-d under several conditions revealed some characteristic features. (a) Antimony pentachloride or chlorosulfonic acid catalyzed the interconversion of the exo-endo ozonide isomers, the ratio in equilibrium being ca. 7:3 for all the pairs. (b) In the reaction of 3-methyl-substituted indene ozonides 2c,d and 3c,d in acetic-d3 acid-d a rapid hydrogen-deuterium exchange on the bridgehead methyl was observed. (c) In methylene chloride or acetic acid the ozonides decomposed very slowly, yielding the mixtures of rearranged products 4 and 5, carboxylic acid 6, and diketone 7; both the rate of decomposition and the product distribution being a marked function of the structure of the ozonides. (d) Methanol accelerated the decomposition of ozonides, the disappearance following pseudo-first-order kinetics.The rate decreased in the order 3a > 2a > 2b > 2c ca. 3c > 3b.This order was significantly different from the order observed in the reaction in acetic acid: 3b > 3c > 2b > 2c > 3a > 2a. (e) Reduction by AlHCl2 gave a mixture of 3,4-dihydro-1H-2-benzopyrans 19 - 22, the composition being significantly varied depending on the stereochemistry of the ozonides. (f) Treatment of 2a or 3a with bis(α-hydroxy-4-methylbenzyl)peroxide (31) gave two stereoisomeric peroxides 32a and 33a in roughly equal amounts.In contrast, the reaction of an exo ozonide 2d with a mixture of p-tolualdehyde and 30percent H2O2 (an equivalent of 31) afforded exclusively the corresponding exo peroxide 32d, while the endo isomer 3d gave predominantly the endo peroxide 33d.