34857-71-1

Upstream product

• 124-38-9 carbon dioxide 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 109-89-7 diethylamine 
• 402-45-9 4-hydroxybenzotrifluoride 
• 88-10-8 N,N-diethylcarbamyl chloride 

Downstream Products

• 25371-98-6 N-(4-trifluoromethylphenyl)imidazole 
• 67589-15-5 1-(2-hydroxy-5-(trifluoromethyl)phenyl)ethan-1-one 
• 1646630-04-7 N,N-diethyl-2-hydroxy-5-(trifluoromethyl)benzamide 
• 1282034-12-1 N-butyl-N-methyl-4-(trifluoromethyl)benzenamine 
• 113845-68-4 1-(4(-trifluoromethyl)phenyl)pyrrolidine 
• 113845-69-5 4-(4-trifluoromethylphenyl)morpholine 
• 1245824-48-9 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-trifluoromethylphenyl N,N-diethylcarbamate 

Relevant academic research and scientific papers

Oxidative Addition of Aryl Electrophiles to a Prototypical Nickel(0) Complex: Mechanism and Structure/Reactivity Relationships

Detailed kinetic studies of the reaction of a model Ni0 complex with a range of aryl electrophiles have been conducted. The reactions proceed via a fast ligand exchange pre-equilibrium, followed by oxidative addition to produce either [NiIX(dppf)] (and biaryl) or [NiII(Ar)X(dppf)]; the ortho substituent of the aryl halide determines selectivity between these possibilities. A reactivity scale is presented in which a range of substrates is quantitatively ranked in order of the rate at which they undergo oxidative addition. The rate of oxidative addition is loosely correlated to conversion in prototypical cross-coupling reactions. Substrates that lead to NiI products in kinetic experiments produce more homocoupling products under catalytic conditions.

N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst

An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is

A copper-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide using molecular oxygen as the oxidant

A Cu-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide is described for the first time in this paper. The reaction tolerates a wide range of functional groups, providing a convenient protocol for the synthesis of various O-aryl carbamates. The successful development of the transformation was enabled by the use of BF3·OEt2 as the promoter and molecular oxygen as the oxidant. Mechanistic studies suggested that the CuII carbamato complex is involved in the catalytic transformation.

Base-Promoted Coupling of Carbon Dioxide, Amines, and Diaryliodonium Salts: A Phosgene- and Metal-Free Route to O-Aryl Carbamates

A phosgene- and metal-free synthesis of O-aryl carbamates is realized through a three-component coupling of carbon dioxide, amines and diaryliodonium salts. The reaction only requires a base as the promoter, providing access to a diverse array of O-aryl c

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.