779-54-4

Usage

Uses

N-(1-Phenylethyl)aniline can be used as fungicides.

Synthesis Reference(s)

Synthesis, p. 401, 1990 DOI: 10.1055/s-1990-26886Tetrahedron Letters, 31, p. 5547, 1990 DOI: 10.1016/S0040-4039(00)97893-6

Upstream product

• 100-42-5 styrene 
• 142-04-1 aniline hydrochloride 
• 1749-19-5 phenyl(1-phenylethylidene)amine 
• 62-53-3 aniline 
• 98-86-2 acetophenone 
• 49543-94-4 Diethylsilanyl-phenyl-(1-phenyl-ethyl)-amine 
• 768-90-1 1-Adamantyl bromide 
• 917-54-4 methyllithium 
• 538-51-2 benzylidene phenylamine 
• 87876-84-4 (E)-acetophenone-O-ethoxycarbonyloxime 
• 85027-95-8 acetophenone oxime mesylate 
• 100-34-5 benzene diazonium chloride 
• 75-07-0 acetaldehyde 
• 591-51-5 phenyllithium 

Downstream Products

• 102453-60-1 phenyl-(1-phenyl-ethyl)-carbamic acid-(2-diethylamino-ethyl ester) 
• 30432-65-6 N-ethyl-N-(α-methylbenzyl)aniline 
• 1749-19-5 phenyl(1-phenylethylidene)amine 
• 1857-74-5 2,3-diphenylbutane 
• 100-41-4 ethylbenzene 
• 2510-98-7 2,3-diphenyl-2-butene 
• 28534-06-7 2-(1-phenylethyl)benzenamine 
• 7476-71-3 4-(1-phenylethyl)aniline 
• 62-53-3 aniline 
• 1749-19-5 N-(1-phenylethylidene)aniline 
• 471254-27-0 C₁₄H₁₄⁽²⁾HN 
• 601505-62-8 C₁₄H₁₃⁽²⁾H₂N 
• 916165-78-1 [2,3,4,5-Ph4(η4-C4CO)Ru(CO)2NH(Ph)(CHCH3Ph)] 
• 1332709-30-4 3-phenyl-1-(1-phenylethyl)indolin-2-one 

Relevant academic research and scientific papers

Isotope effects and the nature of stereo- and regioselectivity in hydroaminations of vinylarenes catalyzed by palladium(II)-diphosphine complexes

(Equation Presented) The hydroamination of styrene with aniline catalyzed by phosphine-ligated palladium triflates exhibits a substantial 13C isotope effect at the benzylic carbon. This supports rate-determining nucleophilic attack of amine on a η3-phenethyl palladium complex. Deuterium exchange observations and predicted isotope effects based on DFT calculations support this mechanism. Selectivity in these reactions is determined by the facility of palladium displacement after reversible hydropalladation of the alkene.

Double [3 + 2]-dimerisation cascade synthesis of bis(triazolyl)bisphosphanes, a new scaffold for bidentate bisphosphanes

A highly convergent synthesis of bis(triazolylphosphane oxides) was developed by a tandem copper-mediated Huisgen reaction-oxidative coupling. The phosphane oxides were reduced by trichlorosilane and the coordination of the resulting bisphosphanes was stu

Measurements of Heavy-Atom Isotope Effects Using 1H NMR Spectroscopy

A novel method for measuring heavy-atom KIEs for magnetically active isotopes using 1H NMR is presented. It takes advantage of the resonance split of the protons coupled with the heavy atom in the 1H spectrum. The method is validated by the example of the 13C-KIE on the hydroamination of styrene with aniline, catalyzed by phosphine-ligated palladium triflates.

Synthesis and structural characterization of palladium dicarbene complexes bearing labile co-ligands

Dicarbene complexes [Pd(OAc)2(diNHC)] (2), [Pd(O 2CCF3)2(diNHC)] (3), and [Pd(CNCH 3)2(diNHC)](SO3CF3)2 (4) bearing labile acetato, fluoroacetato, and aceto

Cyclometalation of (2 R,5 R)-2,5-diphenylpyrrolidine and 2-phenyl-2-imidazoline ligands with half-sandwich iridium(III) and rhodium(III) complexes

Cyclometalation of (2R,5R)-2,5-diphenylpyrrolidine (1) with [(η5-Cp)MCl2]2 using NaOAc in CH 2Cl2 at room temperature, followed by cationization with KPF6 in CH3CN, cleanly yield

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.

Photocatalytic one-pot multidirectional N-alkylation over Pt/D-TiO2/Ti3C2: Ti3C2-based short-range directional charge transmission

Visible-light-induced one-pot, multistep, and chemoselectivity adjustable reactions highlight the economical, sustainable, and green process. Herein, we report Pt nanoparticles dispersed on S and N co-doped titanium dioxide/titanium carbide (MXene) (3%Pt/

Chan-Lam Amination of Secondary and Tertiary Benzylic Boronic Esters

We report a Chan-Lam coupling reaction of benzylic and allylic boronic esters with primary and secondary anilines to form valuable alkyl amine products. Both secondary and tertiary boronic esters can be used as coupling partners, with mono-alkylation of the aniline occurring selectively. This is a rare example of a transition-metal-mediated transformation of a tertiary alkylboron reagent. Initial investigation into the reaction mechanism suggests that transmetalation from B to Cu occurs through a single-electron, rather than a two-electron process.

Cleavage∕cross-coupling strategy for converting β-O-4 linkage lignin model compounds into high valued benzyl amines via dual C–O bond cleavage

Lignin is the most recalcitrant of the three components of lignocellulosic biomass. The strength and stability of the linkages have long been a great challenge for the degradation and valorization of lignin biomass to obtain bio-fuels and commercial chemicals. Up to now, the selective cleavage of C–O linkages of lignin to afford chemicals contains only C, H and O atoms. Our group has developed a cleavage/cross-coupling strategy for converting 4-O-5 linkage lignin model compounds into high value-added compounds. Herein, we present a palladium-catalyzed cleavage/cross-coupling of the β-O-4 lignin model compounds with amines via dual C–O bond cleavage for the preparation of benzyl amine compounds and phenols.

Sustainable Production of Benzylamines from Lignin

Catalytic conversion of lignin into heteroatom functionalized chemicals is of great importance to bring the biorefinery concept into reality. Herein, a new strategy was designed for direct transformation of lignin β-O-4 model compounds into benzylamines and phenols in moderate to excellent yields in the presence of organic amines. The transformation involves dehydrogenation of Cα?OH, hydrogenolysis of the Cβ?O bond and reductive amination in the presence of Pd/C catalyst. Experimental data suggest that the dehydrogenation reaction proceeds over the other two reactions and secondary amines serve as both reducing agents and amine sources in the transformation. Moreover, the concept of “lignin to benzylamines” was demonstrated by a two-step process. This work represents a first example of synthesis of benzylamines from lignin, thus providing a new opportunity for the sustainable synthesis of benzylamines from renewable biomass, and expanding the products pool of biomass conversion to meet future biorefinery demands.