33617-65-1

Upstream product

• 513-36-0 isobutyryl chloride 
• 135-19-3 β-naphthol 
• 79-31-2 isobutyric Acid 
• 97-72-3 2-Methylpropionic anhydride 
• 79-30-1 isobutyryl chloride 

Downstream Products

• 1638677-40-3 2-(naphthalen-2-yl)-1,2-diphenylethan-1-one 
• 612-94-2 2-phenylnaphthalene 

Relevant academic research and scientific papers

Nickel-Mediated Trifluoromethylation of Phenol Derivatives by Aryl C?O Bond Activation

The increasing pharmaceutical importance of trifluoromethylarenes has stimulated the development of more efficient trifluoromethylation reactions. Tremendous efforts have focused on copper- and palladium-mediated/catalyzed trifluoromethylation of aryl halides. In contrast, no general method exists for the conversion of widely available inert electrophiles, such as phenol derivatives, into the corresponding trifluoromethylated arenes. Reported herein is a practical nickel-mediated trifluoromethylation of phenol derivatives with readily available trimethyl(trifluoromethyl)silane (TMSCF3). The strategy relies on PMe3-promoted oxidative addition and transmetalation, and CCl3CN-induced reductive elimination. The broad utility of this transformation has been demonstrated through the direct incorporation of trifluoromethyl into aromatic and heteroaromatic systems, including biorelevant compounds.

Hafnium inspired activation of highly hindered anhydrides in the acylation of alcohols and polyols

A novel and highly efficient method for activating highly hindered acid anhydrides towards the acylation of alcohols and carbohydrate-derived polyols has been developed. This new method relies on the capacity of the hafnium triflate catalyst Hf(OTf)2 to activate highly hindered acid anhydrides, and to direct the acylation reaction. This new acylation protocol is mild and proceed at room temperature with low catalyst loading. The method is versatile and has been extended to different alcohol substrates with different steric encumbrance as well as carbohydrate-derived polyols to afford the corresponding ester products in good to excellent yields.

Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst

Magnesium bistrifluoromethanesulfonimide catalyzed the acetylation of phenols, alcohols, and thiols under solvent-free conditions at room temperature and in short times. Electron-deficient and sterically hindered phenols provided excellent yields. The catalyst was found to be general for acylation with other anhydrides, such as propionic, isobutyric, pivalic, chloroacetic, and benzoic anhydrides. The rate of acylation was influenced by the electronic and steric factors associated with the anhydride. The reaction with less electrophilic anhydrides (e.g., chloroacetic and benzoic anhydrides) required higher temperature (～80 °C). Chemoselective acetylation, pivalation, and benzoylation took place with acid-sensitive alcohols without any competitive dehydration/rearrangement.

Copper(II) Tetrafluoroborate-Catalyzed Acetylation of Phenols, Thiols, Alcohols, and Amines

Copper(II) tetrafluoroborate efficiently catalyzes acetylation of structurally diverse phenols, alcohols, thiols, and amines with stoichiometric amounts of Ac2O under solvent-free conditions at room temperature. Acid-sensitive alcohols are smoothly acetylated without competitive side reactions. The reaction is influenced by the steric and electronic factors associated with the substrate as well as the anhydride. Acetylation of a sterically hindered substrate requires excess of anhydride and longer time. Acylation with less electrophilic anhydrides affords poor to moderate yields.

Electrostatic catalysis by ionic aggregates: Scope and limitations of Mg(ClO4)2 as acylation catalyst

Alkali and alkaline earth metal perchlorates exhibit electrostatic catalysis in the activation of anhydrides for the acylation reaction. Perchlorates with higher values of the charge-size function of the metal ion exhibit better catalytic activity following the order Mg(ClO4) 2>Ba(ClO4)2>LiClO4. Acylation of structurally diverse phenols, thiols, alcohols, and amines have been carried out with stoichiometric amounts of anhydride at room temperature under solvent free conditions in the presence of catalytic amount of Mg(ClO4) 2. Sterically hindered and electron deficient phenols are efficiently acylated. Acylation with sterically hindered anhydrides such as iso-butyric, pivalic, and benzoic anhydrides are carried out with phenols and alcohols in excellent yields. Acid-sensitive alcohols are acylated in excellent yields without any competitive side reactions.

Indium(III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines

Indium(III) chloride efficiently catalyses the acylation of structurally diverse phenols, alcohols, thiols, and amines under solvent free conditions. Acid sensitive alcohols are smoothly acylated without competitive side reactions. Acylation of 2-hydroxynaphthalene is carried out with carboxylic acids adopting the mixed anhydride protocol using trifluoroacetic anhydride.