405-80-1

Upstream product

• 54540-13-5 phenyl 4-(trifluoromethyl)phenyl ketone oxime 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 62-53-3 aniline 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 100-51-6 benzyl alcohol 
• 98-95-3 nitrobenzene 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 79128-83-9 N-(4-(trifluoromethyl)benzylidene)aniline 
• 455-18-5 4-CF₃C₆H₄CN 
• 455-24-3 4-trifluoromethylbenzoic acid 

Downstream Products

• 1607444-37-0 N-(1-(4-(trifluoromethyl)phenyl)but-3-en-1-yl)aniline 

Relevant academic research and scientific papers

Reusable Co-nanoparticles for general and selectiveN-alkylation of amines and ammonia with alcohols

A general cobalt-catalyzedN-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generatedin situby mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based material, >100 primary, secondary, and tertiary amines includingN-methylamines and selected drug molecules were conveniently prepared starting from inexpensive and easily accessible alcohols and amines or ammonia.

Iron-catalysed hydroboration of non-activated imines and nitriles: Kinetic and mechanistic studies

Iron-catalysed hydroboration of imines and nitriles has been developed under low catalyst loading (1 mol%) in the presence of HBpin. A wide scope of substrate was found to smoothly undergo hydroboration, including electron releasing/withdrawing and haloge

Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion

Aldimines and ketimines containing electron-donating and electron-withdrawing groups can be hydrosilylated with borenium catalysts at as low as 1 mol% catalyst loading at room temperature, providing the corresponding secondary amines in excellent yields. Reactions with 2-phenylquinoline gave the 1,4-hydrosilylquinoline product selectively which can be further functionalized in a one-pot synthesis to give unique γ-amino alcohol derivatives. Control experiments suggest that the borenium ion catalyzes both the hydrosilylation and subsequent addition to the aldehyde.

Synthesis ofN-aryl amines enabled by photocatalytic dehydrogenation

Catalytic dehydrogenation (CD)viavisible-light photoredox catalysis provides an efficient route for the synthesis of aromatic compounds. However, access toN-aryl amines, which are widely utilized synthetic moieties,viavisible-light-induced CD remains a significant challenge, because of the difficulty in controlling the reactivity of amines under photocatalytic conditions. Here, the visible-light-induced photocatalytic synthesis ofN-aryl amines was achieved by the CD of allylic amines. The unusual strategy using C6F5I as an hydrogen-atom acceptor enables the mild and controlled CD of amines bearing various functional groups and activated C-H bonds, suppressing side-reaction of the reactiveN-aryl amine products. Thorough mechanistic studies suggest the involvement of single-electron and hydrogen-atom transfers in a well-defined order to provide a synergistic effect in the control of the reactivity. Notably, the back-electron transfer process prevents the desired product from further reacting under oxidative conditions.

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Cooperative catalysis of molybdenum with organocatalysts for distribution of products between amines and imines

Multi-amino groups and nitrogen donors compound was discovered as an organocatalyst for N-alkylation of alcohols with amines in the presence of Mo(CO)6. The Mo(CO)6/organocatalyst binary system has shown to be a highly active catalyst for the N-alkylation reaction between alcohols and amines with excellent tolerance of variable starting materials bearing different functional groups. Of particular note, this method possessing a superiority selectivity in the synthesis of N-alkylated amines or imines, which can be controlled by the reaction temperature. The cooperative catalysis mechanism in combination of Mo(CO)6 with organocatalyst was elucidated by control experiments.

Synthesis of NHC-Iridium(III) Complexes Based on N-Iminoimidazolium Ylides and Their Use for the Amine Alkylation by Borrowing Hydrogen Catalysis

Anionic NHC ligands recently developed in our group, derived from N-iminoimidazolium ylides, were used to synthesize NHC-iridium(III) complexes. Their catalytic activities were evaluated in the amine alkylation of anilines using borrowing hydrogen catalysis. The high-yielding synthesis of a small library of complexes allowed a rapid screening of the ideal steric bulk of the NHC unit and basicity of the anionic tether for the investigated model reaction. A bulky aromatic N group on the imidazolidene moiety is required to achieve high catalytic activity, and the latter is proportional to the basicity of the anionic group. A selected substrate scope of the reaction was performed, providing fair to excellent yields of the desired alkylated anilines.

Quantitative NaH catalytic hydroboration of aldimines

The catalytic hydroboration of aldimines was demonstrated, with only 3 mol% NaH required for the quantitative production of secondary amines under minimal solvent conditions. In addition, chemoselective hydroboration in the presence of other reducible functional groups was achieved. DFT calculations were then used to propose a reaction mechanism for imine hydroboration. This journal is

Lithium bromide: an inexpensive and efficient catalyst for imine hydroboration with pinacolborane at room temperature

An efficient protocol for the hydroboration of imines is reported. Lithium halide salts are effective catalysts to convert aldimines and ketimines to their corresponding amines. Here, we report excellent isolated yield of secondary amines (>95%) using 3 mol% lithium bromide in THF at room temperature. In addition, DFT calculations for a plausible reaction pathway are reported.

Chemoselective Reductive Aminations in Aqueous Nanoreactors Using Parts per Million Level Pd/C Catalysis

Condensation in recyclable water between aldehydes or ketones and amines occurs smoothly within the hydrophobic cores of nanomicelles, resulting in imine formation that is subject to subsequent reduction leading, overall, to reductive amination. This micellar technology enables the synthesis of several types of pharmaceuticals, a new procedure that relies on only 2000 ppm (0.20 mol %) palladium from commercially available Pd/C. A broad range of substrates can be used under mild conditions, leading to high chemical yields of the desired secondary and tertiary amines.