92106-65-5

Upstream product

• 615-42-9 1,2-Diiodobenzene 
• 98-86-2 acetophenone 
• 532-28-5 (RS)-mandelonitrile 
• 451-40-1 phenyl benzyl ketone 
• 615-37-2 ortho-methylphenyl iodide 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 4809-08-9 3-phenyl-isocoumarin 

Relevant academic research and scientific papers

Reactions of o-iodohalobenzenes with carbanions of aromatic ketones. Synthesis of 1-aryl-2-(o-halophenyl)ethanones

o-Iodohalobenzenes (X = I, Br, Cl) react in DMSO with the enolate ions of acetophenone, propiophenone and 1-(2-naphthyl)ethanone to afford mainly monosubstitution with retention of one halogen. The monosubstituted dehalogenated compounds are formed in low overall yields in the reactions of o-diiodobenzene with the carbanions of 1-(2-naphthyl)ethanone and of acetophenone and in the reaction of o-bromoiodobenzene with the carbanion of propiophenone. The reactions can be performed in the dark, with usually increased yields of substitution under irradiation, as well as under FeBr2 initiation. Treatment of 2-(2-bromophenyl)-1-phenylethanone with Cu bronze affords the ring closure benzofuran product. The degree of dehalogenation is discussed in terms of the energetics of the intramolecular electron transfer (ET) from the ArCO-π system to the C-halogen σ bond in the monosubstituted radical anions proposed as intermediates. The lack of ring closure of the radicals formed by dehalogenation of these radical anions is analyzed in terms of geometric factors.

Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+System

Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple methyl benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alcohol products. This finding greatly increases the practicality and impact of this chemistry. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.

Aromatic ring ortho-iodoalkanone and synthesis method and application thereof

The invention discloses aromatic ring ortho-iodoalkanone and a synthesis method and application thereof. The structural formula of the aromatic ring ortho-iodoalkanone is shown in the specification, Ais alkyl or a 5-12-membered ring, R is alkyl, halogen, alkoxy or aryl and R' is hydrogen, alkyl, alkoxy, aryl, substituted aryl or condensed aromatic ring. The synthesis method comprises the step ofreacting with an iodination reagent in the presence of an oxidant to obtain the aromatic ring ortho-iodoalkanone. According to the method, the cheap high-valence iodine reagent is used as an oxidizingagent, the synthesis of the aromatic ring ortho-iodoalkanone can be economically and efficiently realized, the reaction process is simple, safe and easy to operate, the synthesis yield is high, and the method is suitable for industrial production.

Transition-Metal-Free Site-Selective γ-C(sp2)-H Monoiodination of Arenes Directed by an Aliphatic Keto Group

A general γ-C(sp2)-H iodination method directed by an aliphatic keto group has been developed under transition-metal-free conditions for the first time, generating iodoarenes in good to excellent yields with excellent site selectivity. This protocol features a wide range of aryl-substituted ketones, short reaction times, mild reaction conditions, and scalable synthetic procedures. A possible reaction mechanism was also proposed based on several control experiments.

An expedient route to heterocycles through α-arylation of ketones and arylamides by microwave induced thermal SRN1 reactions

Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electron transfer process to form new C-C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse 2-aryl-1- phenylethanones can be prepared by the direct α-arylation of acetophenone with different haloarenes. The ketone enolate anion is generated by deprotonation with tBuOK in DMSO and the reaction is carried out in a closed microwave vessel at 70-100°C for 10 min. This simple procedure also allows the synthesis of deoxybenzoin and indole heterocycle derivatives by inter- or intra-molecular ring closure reactions, with moderate to excellent substitution yields. This journal is the Partner Organisations 2014.

Palladium-catalyzed carbonylative cyclization via trapping of acylpalladium derivatives with internal enolates. Its scope and factors affecting the C-to-O ratio

The Pd-catalyzed carbonylative cyclization reaction involving ω-acyl-substituted acylpalladium derivatives can proceed via intramolecular trapping with either C- or O-enolates; the preferential formation of either 5- or 6-membered rings dictates the C-to-