5706-87-6

Upstream product

• 581-55-5 benzylidene 1,1-diacetate 
• 75-26-3 isopropyl bromide 
• 538-93-2 1-phenyl-2-methylpropane 
• 64-19-7 acetic acid 
• 611-69-8 rac-2-methyl-1-phenylpropan-1-ol 
• 108-24-7 acetic anhydride 
• 611-70-1 phenyl isopropyl ketone 
• 75-36-5 acetyl chloride 
• 873-66-5 1-propenylbenzene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 127-09-3 sodium acetate 
• 546-67-8 lead(IV) tetraacetate 

Downstream Products

• 14898-86-3 (R)-2-methyl-1-phenylpropan-1-ol 

Relevant academic research and scientific papers

Selective benzylic C–H monooxygenation mediated by iodine oxides

A method for the selective monooxdiation of secondary benzylic C–H bonds is described using an N-oxyl catalyst and a hypervalent iodine species as a terminal oxidant. Combinations of ammonium iodate and catalytic N-hydroxyphthalimide (NHPI) were shown to be effective in the selective oxidation of n-butylbenzene directly to 1-phenylbutyl acetate in high yield (86%). This method shows moderate substrate tolerance in the oxygenation of substrates containing secondary benzylic C–H bonds, yielding the corresponding benzylic acetates in good to moderate yield. Tertiary benzylic C–H bonds were shown to be unreactive under similar conditions, despite the weaker C–H bond. A preliminary mechanistic analysis suggests that this NHPI-iodate system is functioning by a radical-based mechanism where iodine generated in situ captures formed benzylic radicals. The benzylic iodide intermediate then solvolyzes to yield the product ester.

Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency

A practical method for the nucleophilic substitution (SN) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric promotor in an invertive SN-type transformation is demonstrated for the first time. The operationally straightforward protocol exhibits high levels of stereoselectivity and scalability and tolerates a variety of functional groups.

Expanding substrate scope of lipase-catalyzed transesterification by the utilization of liquid carbon dioxide

Secondary alcohols having bulky substituents on both sides of the chiral center are often poor substrates for most lipases. Here we reported that substrate scopes of two of the most used lipases, Candida antarctica lipase B and Burkholderia cepacia lipase, were found to be expanded toward more bulky secondary alcohols such as 1-phenyl-1-dodecanol and 2-methyl-1-phenyl-1-propanol by simply using them in liquid carbon dioxide as a solvent. The effects of solvents, reaction pressure, and pre-treatment of the enzyme with liquid CO2on this acceleration phenomenon were also studied.

Alkene Oxyalkylation Enabled by Merging Rhenium Catalysis with Hypervalent Iodine(III) Reagents via Decarboxylation

Rhenium-catalyzed oxyalkylation of alkenes is described, where hypervalent iodine(III) reagents derived from widely occurring aliphatic carboxylic acids were used as, for the first time, not only an oxygenation source but also an alkylation source via decarboxylation. The reaction also features a wide substrate scope, totally regiospecific difunctionalization, mild reaction conditions, and ready availability of both substrates. Mechanistic studies revealed a decarboxylation/radical-addition/cation-trapping cascade operating in the reaction.

NaIO4-mediated C-H activation of alkylbenzenes and alkanes with LiBr

NaIO4 oxidizes lithium bromide efficiently under acidic conditions to functionalize alkylbenzenes and alkanes and produce the corresponding bromo and acetoxy derivatives in excellent yields. The protocol also demonstrates the direct conversion of cyclohexane into trans-1,2- dibromocyclohexane in moderate yield.

Selective functionalisation of hydrocarbons by nitric acid and aerobic oxidation catalysed by N-hydroxyphthalimide and iodine under mild conditions

Alkylbenzenes are selectively functionalised to the corresponding acetates by nitric aerobic oxidation catalysed by N-hydroxyphthalimide and iodine. With cyclohexane the oxidation leads to a mixture of cyclohexyl acetate and trans-2-iodocyclohexyl acetate. The mechanism is discussed.

A new nucleophilic catalyst for kinetic resolution of racemic sec-alcohols

A new tertiary amine-based nucleophilic catalyst, derived from a simple combination of commercially available compounds, affords good to excellent kinetic resolution of racemic sec-alcohols.

First Ritter-type reaction of alkylbenzenes using N-hydroxyphthalimide as a key catalyst

The first Ritter-type reaction of alkylbenzenes with nitriles has been successfully achieved by the use of N-hydroxyphthalimide (NHPI) as a key catalyst. Thus, treatment of ethylbenzene with ammonium hexanitratocerate(IV) (CAN) in the presence of a catalytic amount of NHPI in EtCN under argon produced the corresponding amide in good selectivity.

The chemistry of acylals. Part I. The reactivity of acylals towards Grignard and organolithium reagents

Aldehyde acylals have been prepared and reacted with Grignard and alkyllithium reagents. Acylals from formaldehyde furnished complex reaction mixtures when reacted with both reagents. Acylals of other aldehydes gave reaction mixtures that consisted mainly of an ester, generated by replacing one of the carboxy groups with the organic part of the organometallic reagent, and regenerated aldehyde. The esters were formed in the highest yields. Yields above 90% were experienced when the acylals were reacted with Grignard reagents under Barbier conditions.

The Site of the Sonochemically-Initiated Radical Reaction of Lead Tetraacetate with β-Methylstyrene

The effective temperature of the radical propagation step of the ultrasonically accelerated reaction of lead tetraacetate with β-methylstyrene was thermodynamically determined as close to the ambient temperature of the bulk liquid.