166539-79-3

Upstream product

• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 188837-53-8 (2,3,4,5,6-pentafluorophenyl)pyridine-2-carboxylate 
• 455-24-3 4-trifluoromethylbenzoic acid 

Downstream Products

• 724434-37-1 2-phenyl-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole 
• 447431-60-9 (pyrrolidin-1-yl)(4-(trifluoromethyl)phenyl)methanone 
• 728-86-9 phenyl[4-(trifluoromethyl)phenyl]methanone 
• 25771-21-5 N,N-dimethyl 4-(trifluoromethyl)benzamide 
• 1527472-58-7 N-ethyl-N-phenyl-4-(trifluoromethyl)benzamide 
• 771-61-9 2,3,4,5,6-pentafluorophenol 

Relevant academic research and scientific papers

Palladium-catalyzed intermolecular alkene carboacylation via ester C-O bond activation

We report palladium-catalyzed intermolecular carboacylation of alkenes with ester electrophiles and tetraarylborate nucleophiles. Bicyclic alkenes react with a variety of pentafluorophenyl benzoate and alkanoate esters and sodium tetraarylborates to form ketone products in ≤99% yields. These reactions occur in the absence of a directing group and demonstrate esters are competent acyl electrophiles for intermolecular alkene carboacylation reactions.

Formation of 1-hydroxymethylene-1,1-bisphosphinates through the addition of a silylated phosphonite on various trivalent derivatives

An easily handled one-pot synthetic procedure was previously developed for the synthesis of bisphosphinates starting from acyl chlorides. Herein, other trivalent derivatives as acid anhydrides and activated esters were tested to form various bisphosphinates. This modulation of the reactivity can be controlled according to the nature of the acid derivative for the use of sensitive and functionalized substrates.

Aminolysis of aryl ester using tertiary amine as amino donor via c-o and c-n bond activations

An aminolysis reaction between various aryl esters and inert tertiary amines by C-O and C-N bond activations has been developed for the selective synthesis of a broad scope of tertiary amides under neutral and mild conditions. The mechanism may undergo the two key steps of oxidative addition of acyl C-O bond in parent ester and C-N bond cleavage of tertiary amine via an iminium-type intermediate.

Energy-efficient green catalysis: Supported gold nanoparticle-catalyzed aminolysis of esters with inert tertiary amines by C-O and C-N bond activations

Catalyzed by supported gold nanoparticles, an aminolysis reaction between various aryl esters and inert tertiary amines by C-O and C-N bond activations has been developed for the selective synthesis of tertiary amides. Comparison studies indicated that the gold nanoparticles could perform energy-efficient green catalysis at room temperature, whereas Pd(OAc)2 could not.

Transesterification for synthesis of carboxylates using aldehydes as acyl donors via C-H and C-O bond activations

A new type of transesterification between aryl, heteroaryl, alkyl N-heteroarene-2-carboxylates and various aldehydes by C-H and C-O bond activations has been developed for the synthesis of versatile carboxylates. A possible mechanism containing oxidative addition of acyl-O bond in parent ester and radical cleavage of sp2 C-H bond in aldehyde is proposed.

1,3,4-Oxadiazole formation as traceless release in solid phase organic synthesis

Oxadiazoles were generated upon a dehydrative cyclization reaction with 2-acyl hydrazides bound to the polymeric support via one of their N atoms using TFAA as a dehydration agent.

Evidence for an Alternative Mechanism to a Previously Proposed Self-Replicating System

Rebek et al.1,2 have proposed a "self-replicative" mechanism in which the amide product of an ester aminolysis forms a termolecular complex with the ester and amine reactants.In this manner, the product catalyzes its own formation.The evidence for the mechanism lies mainly in a 40-70percent acceleration when product is added externally to the reaction mixture.The system has now been reinvestigated owing, in part, to doubts created by troublesome experimental problems (e.g. small rate enhancements coupled to >/= 35percent unidentified side reactions) and by the entropic unlikehood of the highly constrained termolecular complex.Our new experiments prove that the Rebek mechanism is unnecessary.Thus, the aminolysis of simple naphthoyl and benzoyl esters, both lacking any hydrogen-bonding sites, are catalyzed by the Rebek "template".In the latter case, the reactions were run under the identical conditions used recently by Rebek (2 mM) while monitoring the formation of the major reaction product.Although the benzoyl ester cannot hydrogen-bond to the template, the ester aminolysis is catalyzed by the template to an extent even greater than that observed by Rebek (i.e. 2-fold).The Rebek mechanism, predicted upon ester/template binding, is clearly invalidated by these experiments.An alternative mechanism, involving amide catalysis, is proposed and found consistent with all available data.