18216-74-5

Usage

InChI:InChI=1/C12H16O/c1-10(8-9-11(2)13)12-6-4-3-5-7-12/h3-7,10H,8-9H2,1-2H3

Upstream product

• 106-98-9 1-butylene 
• 75-36-5 acetyl chloride 
• 763-93-9 hex-3-en-2-one 
• 71-43-2 benzene 
• 591-50-4 iodobenzene 
• 17397-24-9 hex-5-en-2-ol 
• 100-42-5 styrene 
• 78-94-4 methyl vinyl ketone 
• 75-24-1 trimethylaluminum 
• 67-64-1 acetone 
• 98-83-9 isopropenylbenzene 
• 34713-70-7 2-Phenylpropanal 
• 174090-36-9 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane 
• 1459-00-3 1-bromo-2-phenylpropane 

Downstream Products

• 16433-43-5 4-phenyl-1-pentanoic acid 
• 4175-54-6 1,2,3,4-tetrahydro-1,4-dimethylnaphthalene 
• 3548-85-4 rac-2,5-diphenylhexane 

Relevant academic research and scientific papers

C(sp3)-H bond functionalization with styrenesviahydrogen-atom transfer to an aqueous hydroxyl radical under photocatalysis

The redox-neutral addition of α-C-H bonds of acetonitrile and acetone to styrenes was enabledviathe hydrogen-atom transfer from relatively acidic and water-miscible C(sp3)-H bonds to an aqueous hydroxyl radical generated cleanly and iteratively

Aldehydes as Alkylating Agents for Ketones

Common and non-toxic aldehydes are proposed as reagents for alkylation of ketones instead of carcinogenic alkyl halides. The developed reductive alkylation reaction proceeds in the presence of the commercially available ruthenium catalyst [(cymene)RuCl2]2 (as low as 250 ppm) and carbon monoxide as the reducing agent. The reaction works well for a broad substrate scope, including aromatic and aliphatic aldehydes and ketones. It can be carried out without a solvent and often gives nearly quantitative yields of the products. This straightforward and cost-effective method is promising not only for laboratory application but also for industry, which produces carbon monoxide as a large-scale waste product.

A hydrate salt-promoted reductive coupling reaction of nitrodienes with unactivated alkenes

Transition metal-catalyzed reductive coupling has emerged as a powerful method for the construction of C-C bonds. Herein, a crystalline hydrate, Na2HPO4·7H2O, has been disclosed as an effective promoter for the reductive c

A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters

We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin-3-ol or 4-dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron-deficient olefins via radical addition to efficiently form C?C coupled products in a redox-neutral fashion. The Lewis base catalyst was shown to form a redox-active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution.

A practical and catalytic reductive olefin coupling

A redox-economic method for the direct coupling of olefins that uses an inexpensive iron catalyst and a silane reducing agent is reported. Thus, unactivated olefins can be joined directly to electron-deficient olefins in both intra- and intermolecular settings to generate hindered bicyclic systems, vicinal quaternary centers, and even cyclopropanes in good yield. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. Most importantly, it allows access to many compounds that would be difficult or perhaps impossible to access using other methods.

Regioselective ring-opening of cyclopropyl ketones with organometallic reagents

Regioselective ring-opening reaction of cyclopropyl ketones was conducted successfully, in which the reaction of cyclopropyl phenyl ketone with trimethylaluminum catalyzed by nickel acetyl-acetonate gave the ring-opening product in up to 76% yield.

Copper-Catalyzed Conjugate Additions of Organozirconocenes. Synthetic and Mechanistic Studies.

In the presence of 3-10 mol percent of Cu(I) salts such as CuBr*SMe2 or CuCN, alkylzirconocenes add readily to α,β-unsatuatred ketones, aldehydes, and sulfones.The reaction yield is sensitive to the presence of Lewis acids and bases.Steric hindrance as well as a broad range of functional groups are tolerated in the conjugate addition process.Unsaturated N-acyl oxazolidinones give high diastereoselectivities for the formation of the new asymmetric carbon.The resulting zirconium enolates can be used for tandem aldol addition reactions to aldehydes.Depending on the type of copper salt used, slow or fast formation of copper mirror occurs, but no intermediate copper species is detected spectroscopically.Therefore, a mechanism involving enone complexation by the Lewis-acidic zirconocene followed by inner-spere transfer of the alkyl substituent to chelated Cu(I) is proposed.

Electroreductive Intramolecular Coupling of Nonconjugated Aromatic Ketones

The electroreduction of nonconjugated aromatic ketones gave intramolecularly coupled products.The best result was obtained using an Sn cathode in i-PrOH containing tetraalkylammonium salt as a supporting electrolyte.This reductive cyclization proceeded with remarkable stereoselectivity, and the cis isomer was obtained exclusively.A variety of new bi- and polycyclic compounds were synthesized.The reaction mechanism was studied, and it was suggested that the anion radical generated by one-electron transfer to a carbonyl group attacks an aromatic ring intramolecularly.The choice of counter cation of the anion radical was critical for the reductive cyclization.Other reductive methods employing metal reducing agents were also studied.Reduction with Na in HMPA-THF gave the same cyclized product, though the yield was lower than that with the electroreduction.

Transmetalation Reactions of Alkylzirconocenes: Copper-Catalyzed Conjugate Addition to Enones

Rapid hydrozirconation of alkenes by zirconocene hydrochloride, followed by addition of 1 equiv of enone and catalytic amounts of Cu(I) salts, led to the corresponding 1,4-addition products in moderate to high yields and provided the first protocol for in situ preparation of alkyl cuprates from alkenes.

Synthesis of aryl-substituted aldehydes and ketones via palladium-catalyzed coupling of aryl halides and non-allylic unsaturated alcohols

The palladium-catalyzed coupling of aryl halides and non-allylic unsaturated alcohols affords excellent yields of aryl-substituted aldehydes and ketones.