61593-17-7

Usage

InChI:InChI=1/C11H13ClO/c1-11(2,3)10(13)8-6-4-5-7-9(8)12/h4-7H,1-3H3

Upstream product

• 2259-30-5 tert-butylmagnesium bromide 
• 609-65-4 o-chlorobenzoyl chloride 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 74-88-4 methyl iodide 
• 3282-30-2 pivaloyl chloride 
• 108-90-7 chlorobenzene 
• 938-16-9 2,2-dimethylpropiophenone 
• 873-32-5 2-Chlorobenzonitrile 
• 677-22-5 tert-butylmagnesium chloride 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 694-80-4 2-bromo-1-chlorobenzene 

Downstream Products

• 61593-16-6 1-Chloro-2-(2,2-dimethyl-1-phenyl-propyl)-benzene 
• 10489-28-8 2,2-dimethyl-indan-1-one 
• 61593-06-4 1-(2-Chlorphenyl)-1-phenyl-2,2-dimethylpropanol-1 

Relevant academic research and scientific papers

Synergistic interplay of a non-heme iron catalyst and amino acid coligands in H2O2 activation for asymmetric epoxidation of α-alkyl-substituted styrenes

Highly enantioselective epoxidation of α-substituted styrenes with aqueous H2O2 is described by using a chiral iron complex as the catalyst and N-protected amino acids (AAs) as coligands. The amino acids synergistically cooperate with the iron center in promoting an efficient activation of H2O2 to catalyze epoxidation of this challenging class of substrates with good yields and stereoselectivities (up to 97% ee) in short reaction times.

Regio- and chemoselective C-H chlorination/bromination of electron-deficient arenes by weak coordination and study of relative directing-group abilities

It's all relative: A practical and efficient PdII-catalyzed regio- and chemoselective chlorination/bromination has been developed for the facile synthesis of a broad range of aromatic chlorides. The reaction demonstrates excellent reactivity, good functional-group tolerance, and high yields. A preliminary study was conducted to evaluate relative directing-group abilities of various functionalities. Copyright

Ultrasound assisted Friedel-Crafts acylation of aromatics using ferric sulphate as catalyst

The use of ultrasound in the acylation reactions of various aromatics and polyaromatics with different acyl chlorides, in the presence of catalytic amount of ferric sulphate at room temperature, gives good yields of the respective ketones with a short reaction time. A facile and simple synthesis of various aromatic ketones using Friedel-Crafts acylation has been established from the corresponding acid chlorides and aromatic or polyaromatic compounds, respectively under mild reaction conditions with shorter reaction times (30-45 min) and in reasonable yields. This method offers the advantage of low cost and ease of purification of the products because of the small amount of ferric sulphate used in these reactions.

Intramolecular palladium-catalyzed alkane C-H arylation from aryl chlorides

The first examples of efficient and general palladium-catalyzed intramolecular C(sp3)-H arylation of (hetero)aryl chlorides, giving rise to a variety of valuable cyclobutarenes, indanes, indolines, dihydrobenzofurans, and indanones, are described. The use of aryl and heteroaryl chlorides significantly improves the scope of C(sp3)-H arylation by facilitating the preparation of reaction substrates. Careful optimization studies have shown that the palladium ligand and the base/solvent combination are crucial to obtaining the desired class of product in high yields. Overall, three sets of reaction conditions employing PtBu3, PCyp3, or PCy3 as the palladium ligand and K 2CO3/DMF or Cs2CO3/pivalic acid/mesitylene as the base/solvent combination allowed five different classes of products to be accessed using this methodology. In total, more than 40 examples of C-H arylation have been performed successfully. When several types of C(sp3)-H bond were present in the substrate, the arylation was found to occur regioselectively at primary C-H bonds vs secondary or tertiary positions. In addition, in the presence of several primary C-H bonds, selectivity trends correlate with the size of the palladacyclic intermediate, with five-membered rings being favored over six- and seven-membered rings. Regio- and diastereoselectivity issues were studied computationally in the prototypal case of indane formation. DFT(B3PW91) calculations demonstrated that C-H activation is the rate-determining step and that the creation of a C-H agostic interaction, increasing the acidity of a geminal C-H bond, is a critical factor for the regiochemistry control.

Insertion of arynes into carbon-halogen σ-bonds: Regioselective acylation of aromatic rings

Arynes were found to insert into carbon-halogen σ-bonds of various acid halides, enabling acyl and halogen moieties to be introduced simultaneously into adjacent positions of aromatic rings. The Royal Society of Chemistry.

Cobalt-catalyzed cross-coupling reactions of heterocyclic chlorides with arylmagnesium halides and of polyfunctionalized arylcopper reagents with aryl bromides, chlorides, fluorides and tosylates

A range of aromatic organocopper or organomagnesium compounds undergo smooth cross-coupling reactions with aryl bromides, chlorides, fluorides and tosylates, leading to polyfunctionalized aromatics or heterocycles in the presence of cobalt salts (5-7.5 mol%) as catalysts. Very mild reaction conditions are needed and, in the case of cross-coupling with organocopper compounds, Bu4NI (1 equiv) and 4-fluorostyrene (20 mol%) are essential as promoters for successful couplings. Georg Thieme Verlag Stuttgart.

Unexpected cross-coupling reaction between o-chloroaryl ketones and organomanganese reagents

(Chemical equation presented) Alkyl- and arylmanganese reagents react with o-chloro or o-bromoaryl ketones to give the substituted ketones in high yields. The cross-coupling reaction is performed under mild conditions (-60 to +40°C, 30 min to 4 h) and tak