76691-97-9

Upstream product

• 3277-89-2 phenethylmagnesium bromide 
• 62723-78-8 2-methoxymethylaniline 
• 109-89-7 diethylamine 
• 164398-38-3 2-(3-Phenylpropyl)phenyl azide 
• 17082-12-1 trans-azobenzene 
• 53213-26-6 (2-phenylethyl)triphenylphosphonium bromide 
• 552-89-6 2-nitro-benzaldehyde 
• 166329-43-7 N-tert-butoxycarbonyl-2-bromomethylaniline 
• 250643-76-6 tris((2-phenyl)ethynyl)indium 
• 1159987-17-3 2-(3-phenylprop-2-ynyl)aniline 
• 1159987-56-0 C₂₀H₂₁NO₂ 
• 606146-17-2 2-(3-phenylprop-1-yn-1-yl)aniline 
• 10147-11-2 propargyl benzene 
• 615-36-1 2-bromoaniline 

Downstream Products

• 101089-28-5 1-(2-iodophenyl)-3-phenylpropane 
• 93722-90-8 N,N-dimethyl-2-(3-phenyl-propyl)-aniline 
• 164398-38-3 2-(3-Phenylpropyl)phenyl azide 
• 24005-23-0 2-phenyl-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Modular metal-free catalytic radical annulation of cyclic diaryliodoniums to access π-extended arenes

Polycyclic aromatic hydrocarbons (PAHs) are of increasing importance in the advanced material field. Cyclic diaryliodonium salts are non-toxic and environmentally benign arylating reagents. Here, we describe an alkylamine-mediated free radical intramolecular annulation to access PAHs under environmentally friendly conditions. On modulating substituents and their positions in the iodoniums, the free radical reaction controllably underwent three types of cyclization including ring contraction and ring switch to form tricyclic and tetracyclic frameworks of PAHs. Preliminary mechanistic studies implied that alkylamines initiated a radical pathway to complete the cyclization efficiently. Moreover, these acquired products were further converted into diverse complex graphene segments.

A Synthetic Route to Chiral Benzo-Fused N-Heterocycles via Sequential Intramolecular Hydroamination and Asymmetric Hydrogenation of Anilino-Alkynes

An efficient sequential intramolecular hydroamination/asymmetric hydrogenation reaction under catalysis of a single chiral ruthenium complex or a binary system consisting of achiral gold complex and chiral ruthenium complex has been reported. A diverse range of enantioenriched benzo-fused N-heterocycles, including 1,2,3,4-tetrahydroquinoline, indoline, and 2,3,4,5-tetrahydro-1H-benzo[b]azepine derivatives, were obtained from anilino-alkynes in high yields (up to 98%) with moderate to excellent enantioselectivities (up to 98% ee) under mild conditions. This protocol features good functional group tolerance and high atom economy. Furthermore, this catalytic protocol is applicable to gram-scale synthesis of a naturally occurring alkaloid, (-)-Angustureine.

Synthetic method for ortho-alkylaniline

The invention relates to a synthetic method for ortho-alkylaniline. The ortho-alkylaniline is obtained by reduction reaction of ortho-alkyl azobenzene. The reduction reaction is carried out to obtainthe ortho-alkylaniline by the following two modes: the f

Iron-Catalyzed Intramolecular Aminations of C(sp3)?H Bonds in Alkylaryl Azides

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of unactivated C(sp3)?H bonds in alkylaryl azides, which results in the formation of substituted indoline and tetrahydroquinoline derivatives.

Ruthenium-catalyzed meta/ortho-selective C-H alkylation of azoarenes using alkyl bromides

meta/ortho-Selective CAr-H (di)alkylation reactions of azoarenes have been achieved via [Ru(p-cymene)Cl2]2 catalyzed ortho-metalation using various types of alkyl bromides. Particularly, dual meta-alkylation of azoarene and reduction offer an attractive strategy for the synthesis of meta-alkylanilines, which are difficult to access via traditional aniline functionalization methods.

Ionic diamine rhodium complex catalyzed hydroaminomethylation of 2-allylanilines

Ionic diamine rhodium complexes catalyze the hydroaminomethylation of 2-allylanilines. The reaction involves initial hydroformylation followed by reductive amination, which provides direct access to 1,2,3,4- tetrahydroquinolines and 2,3,4,5-1H-1-benzazepi

[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source

The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones have been accomplished in moderate to excellent yields via [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation using aryl azides as nitrogen source.

Reactivities of Nitrenes Generated by Photolysis of 2-(ω-Phenylalkyl)phenyl Azides

In order to investigate the reactivity of a photolytically generated arylnitrene with an intramolecular CH bond, the photochemistry of 2-(ω-phenylalkyl)phenyl azides (1a-d) was examined.Irradiation of 1 in solution revealed that the insertion of the nitrene into an adjacent CH bond to give cyclic compounds 4 and 5 occurs favorably only when a reactive CH bond, such as benzylic, is located close to the nitrenic center.This process can compete with the formation of products derived from triplet nitrene, but not with the capture of didehydroazepine by DEA.On the other hand, irradiation of 1b in an Ar matrix at 12 K gave a mixture of the CH insertion product 4b and the didehydroazepine 15.The origin of the difference in reactivity of the nitrene observed in solutions and in matrix, and the spin state of the nitrene involved in the CH insertion reaction, are discussed.